May Festival

Chester Racecourse, popularly known as 'The Roodee', has the distinction of being the oldest racecourse in operation, according to Guinness World Records, having staged its first recorded race on January 10, 1539. The May Festival, of which luxury jeweller Boodles has been the official, title sponser since 2013, is the most presitigious meeting of the year at Cheshire course. In 2025, the May Festival is schedule for Wednesday, May 7 until Friday, May 9 and, as is customary, consists of Trials Day, Ladies Day and Chester Cup Day. Free Bets UK and other sites will be doubt be helping you make the most of your money.

The Group 3 Chester Vase, run over a mile and half and restricted to three-year-olds, is a recognised trial for the Derby at Epsom on the first Saturday in June and, as such is the feature of a seven-race card on Trials Day. The race was won, by 12 lengths, by the subsequently ill-fated Shergar, en route to a still-record 10-length win on Epsom Downs in 1981, while the most recent participant to win the Derby was Wings Of Eagles, who finished second to stable companion Venice Beach in 2017 before defying odds of 40/1 in the Epsom Classic.

Ladies Day, as the name suggests, is a visual spectactle off the course, but on it the Group 3 Ormonde Stakes, run over an extended mile and five furlongs and open to horses aged four years and upwards, is the undoubted highlight. Notable past winners include Harbinger who, like Shergar, was trained by Sir Michael Stoute and remains, jointly, the ninth highest-rated Flat horse in the history of Timeform.

Again, as the name suggests, Chester Cup Day belongs to the Chester Cup, a 'Heritage Handicap', established, as the Tradesmen's Cup, in 1824, run over an extended two and a quarter miles and open to horses aged four years and upwards. Worth £170,000 in guaranteed prize money, the Chester Cup has a safety limit of 17, but is inevitably over-subscribed. So much so, in fact, that horses balloted out of the main event have an opportunity to contest a consolation event, the Chester Plate Handicap Stakes, run over the same distance as the last race on the card.

Willie Carson

Having been born and raised in Stirling, Scotland, Willie Carson 75, has been an ambassador for horse racing for many years and is a face is familiar to most people living in the United Kingdom. Featuring on television for decades, he was once a team captain of BBC1’s Question of Sport, appearing nationally every Saturday evening.

He earned his name in the sport that he still loves today and his journey began as an apprentice to North Yorkshire based Captain Gerald Armstrong. His first win of note came at Catterick Bridge in the Summer of 1962, when he rode Pinker’s Pond to victory in an apprentice handicap.

Willie Carson learned his trade over the next decade, at which point, he really came to prominence. 10 years after winning his first ever race, he went on to win his first British Champion Jockey title in 1972 and then again in 1973. It was a feat he repeated three more times, coming out on top in 1978, 1980 and 1983.

Ironically, Carson’s best ever tally came 7 years later in 1990, riding to an astonishing total of 187 winners. In many other years, this would have been enough to claim the Champion Jockey mantle, but the imposing figure of Pat Eddery stood in his way and got there first with a staggering 209 winners.

That same season saw Carson become one of just 4 jockeys ever to win 6 winners at the same track on the same day in the whole of the 20th century.

Longevity

Carson always looked after himself and this allowed him to continue until well into his 50s. In 1996, he retired at the age of 54 and was very much still at the top of his game. In 1983, he was deservedly awarded an OBE for his contribution to horseracing and will certainly go down as one of the greats.

Stewards' Cup

Since 1993, the Stewards' Cup has been the betting highlight of the fifth and final day of the Goodwood Festival, a.k.a. 'Glorious Goodwood', staged annually in late July or early August. However, the history of the Stewards' Cup dates back to 1839, when it was conceived by politician and racehorse owner Lord George Bentinck; the inaugural running took place in 1840.

The Stewards' Cup is a Class 2 handicap run over 6 furlongs on the sharp, downhill sprint course at Goodwood and open to horses aged three years and upwards. With total prize money of £250,000, £155,625 of which goes to the winner, the Stewards' Cup is invariably well subscribed. Indeed, with a safety limit of 28, the race often resembles the proverbial 'cavalry charge', at the end of which close finishes and 'shock' results are not uncommon.

A total of five horses have won the Stewards' Cup twice, although the most recent of them was Sky Diver, who did so in 1967 and 1968. Three-time champion jockey Richard Hughes, who retired from race riding in 2015, remains the leading jockey in the history of the Stewards' Cup, with four wins. However, for the leading trainer, we need to look back to the nineteenth century, during which the 'Wizard of the North', John Scott, and James Jewitt both saddled four winners apiece. Down the years, notable winners of the Stewards' Cup have included Soba, Petong, Lochsong, Coastal Bluff and Borderlescott.

Arkle Challenge Trophy

The Arkle Challenge Trophy is a Grade 1 steeplechase run over 1 mile, 7 furlongs and 199 yards on the Old Course at Cheltenham in March. The race is open to horses aged five years and upwards who, at the start of the current season, have yet to win a race over regulation fences. Named after Arkle, who won the Cheltenham Gold Cup three years running, in 1964, 1965 and 1966, the Arkle Challenge Trophy was established, in its current guise, in 1969. Currently scheduled as the second race on the opening day of the Chelteham Festival, the Arkle Challenge Trophy is, in fact, the leading race of its kind in the British National Hunt calendar.

Of course, it follows that the best novice steeplechasers over the minimum trip become the best steeplechasers in open company; in recent years, Moscow Flyer, Azertyuiop, Voy Por Ustedes, Sizing Europe, Sprinter Sacre, Altior and Put The Kettle On have all won the Arkle Challenge Trophy followed by the Queen Mother Champion Chase at the next Cheltenham Festival. Nicky Henderson, trainer of Sprinter Sacre and Altior, also saddled Remittance Man (1991), Travado (1993), Tiutchev (2000), Simonsig (2013) and Shishkin (2021) for a total of seven wins and is the leading handler in the history of the Arkle Challenge Trophy.

Looking forward to the 2023 renewal of the Arkle Challenge Trophy, which is scheduled for 2.10pm on Tuesday, March 14, the ante-post lists are dominated by Jonbon and El Fabiolo, who finished miles clear when first and second in the Top Novices' Hurdle at Aintree, and Sir Gerhard, a comfortable winner of the Ballymore Novices' Hurdle at the Cheltenham Festival. At longer odds, Monmiral, described by trainer Paul Nicholls as 'a proper horse', has always looked an embryonic steeplechaser in the making.