Racing in the Cheltenham area dates back 200 years to 1815 when the first recorded flat racing meeting was held on Nottingham Hill. 

Fortunately, we’ve turned back the years and taken a look at the races and riders that ingrained themselves in Cheltenham history – the likes of which you can read about in our 2023 Cheltenham festival guide.

So, without further ado…

The Early Years (1818 – 1911)

The first races were a tentative affair of which little is recorded and it was a further three years before another meeting was staged, this time on Cleeve Hill which overlooks the current Cheltenham racecourse site. This one-day meeting took place on Tuesday 25th August 1818, including five races and Cheltenham’s first recorded winner, was Mr. E.Jones’ five-year-old bay mare, Miss Tidmarsh.

The Cleeve Hill meeting was evidently a success because the following year saw the construction of a grandstand on the side of the hill which was said to be visible from the Promenade. A proper course was laid on on the West Down of the hill and for 1819 the meeting was increased to three days duration (23-25 August). The main attraction of the final afternoon was the first-ever Cheltenham Gold Cup, a three-mile flat-race for three-year-olds, won by Spectre.

The races on Cleeve Hill soared in popularity over the next decade with crowds of up to 50,000 attending an annual two day July meeting. During this period the races became the central feature of a carnival, in town and on the hill – the elite was attracted to extravagant parties staged in Cheltenham, a fashionable spa town, whilst on the hill sideshows and drinking and gambling booths catered for the masses.

Inevitably the races began to attract some unwelcome elements such as pickpockets, drunkards, cards sharps and prostitutes and further to the ultra-evangelistic Anglican Rector of Cheltenham, Reverend Francis Close, preaching about the evils of horse racing and gambling, such strong feelings were aroused amongst his congregation that the meeting in 1829 was disrupted, with bottles and rocks thrown at the horses and their top jockeys. Before the following year’s meeting, Close was the instigator of an arson attack in which the facilities were burnt to the ground!

As a result, the following year races were moved to Prestbury Park in “three fields” for flat racing around a roughly drawn course, with a 700-capacity grandstand erected. Prestbury Park was first used for racing on 19th July 1831 where it continued until 1834, but the turf was not as good as on the hill and in 1835 the races returned to Cleeve Hill where a new three-story stand had been built and access to the course improved. However, in part due to an economic depression, the glory days of the Cheltenham flat races were over as numbers dwindled and the glamour that initially surrounded it evaporated. The standard of racing on the hill deteriorated and even the renaming of the races in 1840 as the “County of Gloucester Races on Cleeve Hill Course” failed to stop the decline – from 1843 to 1850 there was no flat racing at all and after a brief revival between 1851-1855, there were no further meetings on the hill.

However, just as interest in flat racing diminished, steeplechasing began to become more popular. In 1834 in nearby Andoversford, the first Grand Annual Steeplechase was run over four miles on the open countryside surrounding the town. The race, on Friday 4th April 1834, attracted a field of nine runners and watched by a crowd of around 10,000 that placed their Cheltenham free bets with vigor. Unusually for a steeplechase at this time, the race could be seen in its entirety from the winning field and was won by Fungleman, despite falling at the last fence! In second was Conrad whose effort was particularly noteworthy as the previous day he’d won two races on the Flat over the Prestbury Park course.

Predating the Grand National by two years, the Grand Annual is the oldest race in the jumping calendar and in subsequent years the races were run at various courses including Andoversford, Southam and in 1847 at Prestbury Park in a race won by William Holman on Stanmore with William Archer finishing second on Daddy Longlegs. The race continued to be held in Prestbury Park until the land was sold in 1853 (for £19,600). The new owner was totally opposed to racing and would not have it on his land.

As the century drew to a close racing of all kinds was losing popularity and Cheltenham races seemed destined to die a quiet death, but in 1881 Prestbury Park was sold to Cheltenham Racecourse’s founder, Mr. W.A Baring Bingham, a racing enthusiast who wanted to revive its former glories. However, at first, he used the Park as a stud farm and it was not until 1898 that a race meeting was held there with a modicum of success, re-establishing racing at its current location.

Four years later Prestbury Park held its first National Hunt Festival (9-10 April 1902).

The Cheltenham Festival was originally the National Hunt Meeting – the meeting that staged the National Hunt Chase, the four-miler for amateur riders. This race was first run in 1860 at Market Harborough and regularly changed venue. Held at Prestbury Park in 1904 and 1905 it finally settled there in 1911, where it has remained ever since. As it was the second most prestigious prize in the National Hunt calendar, after the Grand National, the March meeting at which it was run assumed permanent importance from that year.

The Cheltenham Festival

Frederick Cathcart is the man who did more than anyone else to make Cheltenham the headquarters of jump racing. Cathcart was a senior partner of Messrs Pratt & Co, the firm in charge of managing several racecourses including Prestbury Park.

He was to become the most influential racecourse official of the 20th century and guided the fortunes of Cheltenham as both clerk of the course and the founding chairman of The Steeplechase Company (Cheltenham) Ltd.

Cathcart decided that just as Newmarket was for flat racing, so Cheltenham should be established as the headquarters of National Hunt racing.

The first Cheltenham Festival took place at Prestbury Park in 1911 when The National Hunt Committee agreed to terms with The Steeplechase Company to allow the National Hunt Meeting to remain year-on-year at Cheltenham rather than continue its traditional annual tour.

That year the very wet weather spoilt the enjoyment of the huge crowd for the two-day fixture and the going proved exceptionally heavy.

The four-mile National Hunt Steeplechase on the first day, Wednesday, had prize-money of £815 and was won by Sir Halbert by a neck at odds of 33/1. The three-and-a-quarter-mile National Hunt Steeplechase the following day (the forerunner of the Gold Cup) was worth £832 and was raced in heavy hail and sleet. It was won by Autocar at odds of 100/6.

A new stand had been built in that first Festival year of 1911 and a “Luncheon and Private View to Press and Officials” was given on the course beforehand presided over by Cathcart. That little stand, so small and quaint by the standards of Cheltenham today, was to see service for the next 70 years!

The Early Days

Under Cathcart’s direction, the meeting grew significantly in importance and, such was the popularity of the occasion, it was expanded from two days to three in 1923. The following year saw the introduction of a level weight extended three-mile steeplechase, called The Cheltenham Gold Cup followed, in 1927, by The Champion Hurdle.

Frederick Cathcart died in 1934, aged 74. His Sporting Life obituary stated: “He was indefatigable in his efforts to increase the popularity and public appeal of the race meetings with which he was associated…Much of the success of the ‘chasing at Cheltenham was due to Mr. Cathcart’s energy and enterprise.”

All the NH Meetings needed to be was a star to project its appeal to a wider audience who bought Cheltenham tickets in hordes. Golden Miller more than filled that vacancy, winning The Gold Cup five times in the 1930s to become the sport’s first household name.

The first of these wins came in 1932 at just five years old. Better was to follow in 1934, when still at just seven years of age he won both the Gold Cup and the Grand National in the same season – a feat that has never been equaled before or since. His sequence of Gold Cup victories (from 1932-1936) may have been even better had it not been for the 1937 renewal being lost to the weather. He was retired in 1939 with a record of 28 wins from 52 races.

The Post-War Years

The bounce-back following the Second World War came in the form of Cottage Rake, the first Gold Cup winner to be trained in Ireland, who went on to win three and, with Vincent O’Brien at the helm, sparking the Irish invasion that has become the hallmark of the Festival. Timing is everything in sport and three ingredients came together in the 1960s to launch The Festival into the modern era.

The racecourse was bought by Johnny Henderson, the late father of trainer Nicky Henderson, and his city friends to form Racecourse Holdings Trust. This prompted a massive investment, the BBC embracing racing as a key element of its outside broadcast agenda and a horse without parallel carrying all before him.

It is over 40 years since Arkle won three consecutive Cheltenham Gold Cups, but his achievements have stood the test of time and at 212 his Timeform rating is the highest ever awarded to a steeplechaser. Only Flyingbolt, also trained by Tom Dreaper, had a rating anywhere near his at 210. The third highest is Kauto Star & Mill House on 191. Such was his class that when running in handicaps, he was forced to give away huge amounts of weight – yet still managed to come home in front. In his 34 races under rules, he carried at least 12 stones in 23 of them but finished with a career total of 27 victories.

Cheltenham is where true National Hunt champions prove themselves and Arkle was no exception, fittingly making his (winning) chasing debut there in November 1963. He was back for the Festival the following March where he won what is today known as the RSA Chase. The Gold Cup itself was that year won by Mill House and the subsequent rivalry between him and Arkle, billed as a clash between England and Ireland, became one of the most famous of all-time.

When the pair first met in the Hennessy the following season, Mill House prevailed but Arkle had his revenge at Cheltenham in the 1964 Gold Cup. His success in the following two years saw him established as a legend at the course, where he is honored with a special statue.

The Modern Era

The event has continued to gain prominence within the racing calendar both from an entertainment perspective as well as on the betting tips forefront. And it is now widely recognized as one of the UK’s premier sporting events, alongside the likes of Wimbledon, the British Open, the British Grand Prix and the FA Cup Final.

The Dickinson Famous Five and Dawn Run landing the Champion Hurdle/Gold Cup double catapulted The Festival to the front of the nation’s consciousness in the 1980s, a decade that climaxed with Desert Orchid triumphing in conditions that only Cheltenham can muster. Istabraq and then Best Mate brought another generation to claim The Festival as their very own before Kauto Star became the first Cheltenham Gold Cup Champion ever to regain the title in 2009.

The Festival is the county’s biggest single revenue-earning event, generating an estimated £50m for local hotels, shops, pubs, and clubs.

2005 saw the first four-day Festival with six races on each day. A new 3m7f Cross Country Chase was added to Tuesday’s card, which still features the Champion Hurdle. Wednesday’s highlight is still the Queen Mother Champion Chase, while the World (Stayers) Hurdle is now the highlight of Thursday’s card. Friday is now Gold Cup day with the Triumph Hurdle, Foxhunters and County Hurdle still also appearing on the final afternoon. The first four-day Festival was undoubtedly a huge success and the format was retained in 2006 and looks set to stay.

The build-up to Cheltenham now dominates the entire jumps season, with every decent race run after the turn of the year being seen as some form of Festival trial. Some have argued that this is detrimental to other top-class races that are prestigious events in their own right. However, any potential downside is surely outweighed by the fact that the increased interest in the Festival has widened the attraction of national hunt racing on a worldwide basis and has brought thousands of new enthusiasts to the sport. It also provides a climax and focuses that the Flat season so badly lacks.

Each year the attendances have also continued to grow, and over the duration of the meeting, crowds will easily exceed 200,000. Combine this with those watching on television, listening to the radio and following live on-line feeds – which you can read more about in our Cheltenham Festival 2023 guide – and you have, without doubt, one of the world’s most anticipated racing spectacles.

The quality of the entrants for each and every race is top class, and the event seems to have an increasingly international flavor to it each year. Runners from France, Eastern Europe (particularly in the Cross Country Chase) and Germany are becoming more and more common, and are enjoying considerable success.

However, it is the involvement of one nation in particular, both on and off course, which gives the Festival its unique atmosphere.

The Irish and The Festival

The Irish have been traveling to Cheltenham for generations and a huge Irish presence is an essential part of the unique atmosphere every March. It is estimated that about 7,500 to 8,000 people travel from Ireland to the Gloucestershire countryside each year, although this has declined by about 30% for the last couple of Festivals as a result of the economic downturn.

Those who journey are making one of the sport’s great annual pilgrimages, to attend National Hunt racing’s famous four-day spectacle. The Irish regularly take center stage on this great occasion, whether it be man or beast. Some of the greatest jockeys, trainers, owners, and horses to have graced the hallowed turf of Prestbury Park have originated from the Emerald Isle. Legendary Irish names such as Jonjo O’Neill, Dawn Run, Arkle, Vincent O’Brien, and Istabraq have sealed their place in Cheltenham Festival folklore with their glorious achievements at this magnificent course.

The Festival would certainly not be the same without the Irish punters who revel in taking on Cheltenham’s bookmakers. Probably the most famous Irish gambler to be found at the Festival is owner JP McManus, known in racing circles as the “Sundance Kid”, who for more than 20 years has bet – and won – huge sums, including successful wagers on his dual Champion Hurdle winner Istabraq.

Legend tells of another Irishman who won enough on Istabraq in the Champion Hurdle of 1998 to pay off his mortgage and then lost his house on Doran’s Pride in the Gold Cup. “It was only a small house anyway,” he is reputed to have said.

Tragedy mingles with triumph all too closely in National Hunt racing and the Irish have suffered their fair share – such as former jockey Shane Broderick, who was paralyzed after a horrific fall at Fairyhouse in 1997. Despite his disability, he bravely reflected on how lucky he was to ride a winner at Cheltenham. These stories sum up the indomitable spirit of the Irish that characterizes the history of the Cheltenham Festival.

The Emerald Isle re-affirmed their dominance of the National Hunt scene in 2006 by winning the three most prestigious prizes the Cheltenham Festival has to offer. Their success reached a magnificent crescendo on the final day when War of Attrition led home an Irish one – two – three in the Gold Cup to send his countrymen into raptures on St Patrick’s Day.

The emotional win of Moscow Flyer in the Champion Chase in 2005 will also live long in the memory, as the Irish chaser confirmed himself as one of the all-time greats and sparked wild Irish celebrations.

Champions, Cups, and Cancellations

1911: Festival is established.

1924: First Gold Cup is run at the Festival, won by Red Splash with prize money of £685.

1927: First Champion Hurdle.

1932-1936: Golden Miller runs up an amazing sequence of five Gold Cup (in 1934 he became the only horse ever to win the Aintree Grand National and the Cheltenham Gold Cup in the same season).

1948-1950: Cottage Rake’s hat-trick in the Gold Cup marks the birth of the annual pilgrimage from Ireland.

1954: First locally-trained winner, Four Ten, trained in Prestbury by John Roberts.

1963-1965: Arkle’s hat-trick of Gold Cups creates a legend.

1978: Gold Cup is abandoned because of snow and is run in April instead.

1989: Desert Orchid brings the house down by winning the Gold Cup.

1990: Norton’s Coin, at 100-1 the longest-priced winner of the Gold Cup, triumphs in the sunshine for Welsh dairy farmer Sirrell Griffiths.

1997-2000: Istabraq runs up a Festival sequence of four victories, first in what is now the Ballymore Properties Novices Hurdle, then a hat-trick in the Smurfit Kappa Champion Hurdle.

2001: Festival abandoned because of foot and mouth disease.

2002-2004: Best Mate dominates the Gold Cup, the first three-timer since Arkle.

2005: Festival extended from three to four days.

2007: Kauto Star wins the richest ever Totesport Cheltenham Gold Cup and picks up a £1m bonus.

2008: Day two of the Festival canceled due to high winds with all Wednesday races moved to Thursday and Friday.

Cheltenham Festival – Lost Races

Since the first Cheltenham Festival in 1911, a number of races have come and gone or been replaced. Below we detail those lost races of the Cheltenham Festival:

Croome Hunters’ Chase (1911)

Chapilizod, who subsequently won the 1913 Foxhunter Chase, won the only Festival running of this race.

Rose Hill Handicap Hurdle (1911)

Hardingstone, the 5/4 favorite, won the only renewal of this race, which was named after a local beauty spot.

Cheltenham Chase (1911)

Another race that survived only one year at the Festival.

Prestbury Handicap Chase (1911-12)

Although pre-dating the Festival, this race was only staged twice after 1911.

Southam Selling Chase (1911-15, 1921)

A short-lived two-mile chase.

Cotswold NH Flat Race (1911-21)

Run-on six occasions.

Cleeve Selling Hurdle (1911-23)

Staged on eight occasions. The winner in 1911, Aftermath, won the following year’s running of the Stayers’ Selling Hurdle.

Swindon Selling Chase (1911-39)

The only winner of note was Denis Auburn in 1920 who also won the Foxhunters’ Chase in 1915.

National Hunt Juvenile Chase (1911-58)

Perhaps the Festival’s most notorious race, this event – open only to four-year-olds – was finally abandoned in 1958 with the aptly named Bee Off riden by John Lawrence (later Lord Oaksey) winning the last renewal. 

 The most notable winners of this race were future Grand National winners, Grakle and ESB and subsequent Gold Cup victor, Medoc II. In 1959 the race was replaced by the National Hunt Two-Mile Champion Chase, which later became the Queen Mother Champion Chase.

Jubilee Handicap Hurdle (1912)

Staged as a one-off in 1912, the Jubilee was replaced by the County Hurdle in 1913. In effect, the only difference between the two races was the name as the distance and value were exactly the same.

Stayers’ Selling Hurdle (1912-38)

The original Stayers’ Hurdle, which unlike the race currently staged at the Festival, was a seller, was dropped from the Festival program in 1928. It returned in 1930 but was abandoned twice due to bad weather in the ‘thirties. Silver Bay (1913 and 1914), Warwick (1923 and 1925) and Sobrino (1930 and 1933) were all dual winners.

Maiden Five-year-old Chase (1915)

A one-off won by Gary Mac who won the Southam Selling Chase five years later.

Coventry Handicap Chase (1915)

Only one renewal for this 3m 2f chase.

Amateur Riders’ Chase (1920-29)

Run over two miles until 1923 and then three thereafter, the only notable winner was Dudley in 1923.

Breedon Selling Handicap Hurdle (1923-26)

Introduced when the Festival was extended to three days in 1923.

Newent Selling Chase (1923-42)

Run over two miles, The Newent Chase was, for a number of years, the opening race of the Cheltenham Festival. One name stands out from the winners of this race: Ferrens. A selling plate specialist, trained by George Beeby, Ferrens made seven appearances at the Festival, finishing unplaced in the 1933 Seven Springs Chase, second in the 1934 Swindon Chase and third, second, second, first, tenth and second in successive renewals of this from 1935-39. He was fifteen when he won and seventeen when he made his last appearance in 1939.

Spa Hurdle (1923, 1942, 1946-67, 1971)

A Spa Hurdle, over three miles, was run during the 1923 Festival and again in 1942 over two miles. It was established as a stayers’ hurdle from 1946 until 1967, when it transferred to the April meeting in 1968, although it made a fleeting reappearance at the 1971 Festival and was subsequently revived at Cheltenham’s New Year’s Day meeting. 

It was replaced in 1972 at the Festival by the Stayers Hurdle, today known as the World Hurdle. Prominent winners of the Spa Hurdle include the 1955 Champion Hurdler, Clair Soleil, successful in 1959 with legendary jockey Fred Winter. Merry Deal won this aged twelve in 1962, five years after winning the Champion Hurdle. Beau Normand, trained by Bob Turnell, is the only dual winner, having been successful in 1963 and 1967.

United Hunts Challenge Cup (1923-73)

Last run at the Festival in 1973, the race subsequently formed the centerpiece of Cheltenham’s April Hunter’s meeting. Baulking Green’s name will forever be associated with this race. A strong chestnut, owned by Jim Reade and trained by Captain Tim Forster, Baulking Green won this race on four occasions, three times in succession between 1963-65 and again in 1967. 

In 1968, at the age of fifteen, he was beaten a short-head by Snowdra Queen, who had also taken the 1966 renewal. Uppergrange, (1926 and 1928), Cheerful Marcus (1935 and 1936) and Mr Teddy (1959 and 1962) also won the United Hunts Cup twice.

Open Military Handicap Chase (1924-26)

Only run on three occasions. Winner in the first two years was Ruddy Glow, who started favorite for the 1926 Gold Cup but could only finish third.

Cleeve NH Flat Race (1924-26)

Also, run on just three occasions, the final renewal was worth £415.

United Services Hunt Cup (1927-29)

Run over three-and-a-half-miles.

Swindon Hurdle (1928-29)

Replaced the Stayers’ Selling Hurdle for two seasons.

Coventry Cup Chase (1928-36)

Introduced in 1928, the Coventry Cup became an unofficial two-mile championship. Fields were always small but select, although the match won by the 1/5 favorite Rathcoole in 1929 and Thomond II’s walkover in 1934 were taking this selectivity a little too far. The inaugural running went to the fourteen-year-old Dudley, while in 1930 Blaris, the winner of the first Champion Hurdle in 1927, was successful.

Lansdown Selling Handicap Hurdle (1928-42)

No notable winners, with the exception of Anarchist, who had finished second to Seneca in the previous year’s Champion Hurdle and won the Lansdown Hurdle in 1942, a few days before finishing second to Forestation in the Champion Hurdle.

Seven Springs Handicap Chase (1930-50)

Although well established before the war, this race only survived until 1950. Notable winners include Thomond II (a great rival of Golden Miller, who beat him three times in big races – twice in the Gold Cup and once in the Grand National). 

Abbot’s Glance won in 1936 and 1939 whilst Medoc II won successive renewals in 1940 and 1941 before winning the 1942 Gold Cup. Silver Fame, the winner of twenty-seven chases for his owner Lord Stalbridge, won this in 1948, three years before winning the Gold Cup.

Cathcart Challenge Cup Chase (1938-2004)

The two miles and five furlongs Cathcart Chase was a race for novices and second-season chasers named in honor of Frederick Cathcart, the clerk of the course and chairman at Cheltenham from 1908 to 1934. Quita Que (1958 and 1961), Half Free (1985 and 1986) and Stormyfairweather (1999 and 2000) were dual winners of the Cathcart, whilst Fred Winter trained seven winners of the race between 1972-1987. 

It was replaced in 2005 by two separate races: the Jewson Novices Handicap Chase and the Festival Trophy (Ryanair Chase) which were opened up to all horses.

National Hunt Moderate Chase (1941)

Thankfully, the Moderate Chase was only run once at the Festival. Victory, in this two-mile race, went to Uplifter.

High-Class Hurdle (1946)

Flying Mascot won the only running of this two-mile hurdle race in 1946.

High Flyer Chase (1946)

A selling chase over three miles, this race made one appearance at the Festival in 1946 when the Brian Marshall rode Lavenham beat his four rivals.

Gloucestershire Novices’ Hurdle (1946-1973)

Between 1946-1971 the Gloucestershire Hurdle was divided on no less than 25 occasions and in 1946 and 1963 there were even three divisions. From 1974 it was renamed the Lloyds Bank Novices Hurdle, the first of various sponsors of a race that became known as the Supreme Novices’ Hurdle in 1980 when it took its now traditional spot as the Festival opener.

Croome Hurdle (1947)

Run as part of the revised one-day Festival in 1947.

Mildmay of Flete Handicap Chase (1951-2005)

Established in 1951 and originally named in memory of the 2nd Baron Mildmay of Flete (1909–1950), an amateur National Hunt jockey who rode three winners at the Cheltenham Festival. The inaugural race took place in April because it’s planned running in March was abandoned due to waterlogging. The race was renamed The Festival Plate in 2006 and is now known as the Byrne Group Plate.

Birdlip Hurdle (1952-62)

Originally a two-mile selling hurdle, this race was run at the Festival on ten occasions. From 1958 its distance was extended to three-miles. A notable name amongst the winners is Lester Piggot who rode Mull Sack to victory in 1954, whilst Fred Winter rode St Stephen to victory in 1962.

Aldsworth Hurdle (1956, 1971-73)

A race of this name firstly appeared at the Festival in 1956 as a two-mile heat won by Nickleby. It reappeared in 1971 and is now known as the Neptune Investment Management Novices Hurdle.

George Duller Handicap Hurdle (1963-73)

Run in memory of a legendary hurdling specialist (before he turned to motor racing), this three-mile race appeared on eleven occasions and was run in two divisions in 1969. In 1974 it was switched to the April meeting and replaced at the Festival by the Joe Coral Golden Hurdle Final, which is now known as the Pertemps Handicap Hurdle Final.

Cathcart Champion Hunter Chase Challenge Cup (1975-77)

This shortlived race replaced the Cathcart Cup for three seasons. The first renewal, in 1975, was abandoned and the subsequent two runnings went to Mickley Seabright and Rusty Tears. In 1978 the Cathcart reverted to its original name.