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The Cathcart Challenge Cup was inaugurated in 1938 and named in memory of Frederick Cathcart, former Chairman of Cheltenham Racecourse, who died four years earlier, but was responsible for the creation on the Cheltenham Gold Cup, as a steeplechase, in 1924 and the Champion Hurdle in 1927. The race was always a steeplechase, but was run in various guises down the years, including an abortive stint as the Cathcart Champion Hunters’ Chase between 1975 and 1977. Most recently, though, it was a Grade 2 contest, run over 2 miles and 5 furlongs on the New Course at Cheltenham and open to first- and second-season steeplechasers.

The Cathcart Challenge Cup was run for the last time on March 18, 2004 and won by the six-year-old Our Armageddon, trained by Richard Guest and ridden by Larry McGrath, who made all the running to beat Iris Royal by 2½ lengths. The following year, the race was replaced by the Festival Trophy, initially sponsored by the Daily Telegraph, which was open to steeplechasers at all levels of experience. In 2006, Ryanair took over the sponsorship and, two years later, the newly-titled Ryanair Chase was promoted to Grade 1 status; alongside the Stayers’ Hurdle, the Ryanair Chase is one of the feature races on day three of the Cheltenham Festival.

Like its successor, the Cathcart Challenge Cup was a ‘championship’ race over a distance intermediate between that of the Queen Mother Champion Chase and the Cheltenham Gold Cup. For the record, since World War II, the legendary Fred Winter was the leading trainer with seven wins, courtesy of Soloning (1972), Soothsayer (1974), Roller Coaster (1979), Dramatist (1982), Observe (1983) and Half Free (1986 and 1987).

Bred at the Gerrardstown House Stud in Dunshauglin, County Meath, Our Conor was initially campaigned on the Flat by leading Irish jumps trainer Dessie Hughes, winning twice, at Roscommon and Naas, as a three-year-old, in the summer of 2012. Sent over obstacles that autumn, he made a winning debut in a maiden hurdle, again at Naas, justifying odds-on favouritism with an easy, 8½-length victory. He did so again in a Grade 3 juvenile hurdle at Fairyhouse the following month and, the following February, made a seamless transition to the highest level with a comfortable, 5-length defeat of the hitherto unbeaten Diakali, trained by Willie Mullins, in the Grade 1 Spring Juvenile Hurdle at Fairyhouse.

Our Conor subsequently arrived at the Cheltenham Festival boasting a 3-3 record over hurdles and, consequently, was sent off 4/1 joint second favourite for the Triumph Hurdle. Once again, he more than justified his market position, effortlessly drawing clear between the final two flights to win, impressively, by 15 lengths. Unsurprisingly, he was promoted to favouritism for the 2014 Champion Hurdle and, a few days later, sold to leading owner Barry Connell, for an undisclosed sum, although Connell declared himself ‘delighted to have the opportunity to buy him’.

The change of ownership meant that regular jockey Bryan Cooper, who had ridden Our Conor to all four wins over hurdles, was replaced by Danny Mullins, who was retained by Connell. Thereafter, barring a tenderly-handled fourth place on the Flat at Naas, the Jeremy gelding was campaigned exclusively at Grade 1 level over hurdles for the remainder of his tragically short career

However, he never won again. He was beaten by Hurricane Fly in the Ryanair Hurdle and the Irish Champion Hurdle, both at Leopardstown, before crossing swords with the defending champion for the third time in as many starts in the Champion Hurdle proper at Cheltenham. Sent off at 5/1 fourth favourite, he led as far as the third flight, where he took a horrific fall, sustaining a serious back injury. After extensive treatment by veterinary surgeons, he was humanely euthanised.

By his own admission, Martin Pipe ‘never, ever, wanted to be a trainer.’ However, with his brief, less-than-prolific career as an amateur rider cut short by a broken thigh in 1972, Pipe did, indeed, turn his attention to training at a then-derelict farm in Nicholashayne, near Wellington, Somerset two years later. Reflecting on those early days, he once told the ‘Racing Post’, ‘I didn’t know anything about training when I started, I didn’t have a clue.’

After a slow, nay tortoiselike, start, Pipe first attracted the attention of the wider racing public when, in 1981, he saddled his first Cheltenham Festival winner, Baron Blakeney, ridden by Paul Leach, in the Triumph Hurdle. Belying odds of 66/1, Baron Blakeney made relentless progress from the final flight to collar the 7/4 favourite, Broadsword, trained by David Nicholson and ridden by Peter Scudamore, in the closing stages, landing a gamble in the process.

The rest, as they say, is history. Pipe would win the National Hunt Trainers’ Championship for the first in 1988/89, with an eye-watering 208 winners. In the next 17 seasons until his retirement, due to ill health, in April, 2006, he would relinquish the trainers’ title just three times, to David Nicholson in 1993/94 and 1994/95 and to Paul Nicholls (who was winning his first title) in 2005/06.

Unremarkably, Pipe still holds the record for the most trainers’ titles (15) and the most consecutive titles (10) in National Hunt history.

Indeed, his revolutionary, scientific approach to training, coupled with a knack for placing his horses, led Pipe to a career total of 4,191 winners, including several high-profile winners on the Flat. It is difficult to argue with former stable jockey Peter Scudamore, who once said of Pipe, ‘Quite simply, he was a genius of his time.’

Dunkirk remains the seventh highest-rated steeplechaser in the history of Timeform, adjudged just 1lb inferior to Desert Orchid and 2lb superior to Burrough Hill Lad. Yet, when it comes to a discussion of the truly great steeplechasers of the twentieth century, his name is rarely mentioned. That is, perhaps, because he was a direct contemporary of Arkle, Flyingbolt and Mill House, but as ‘one of the most exhilarating sights in racing’, according to Timeform, Dunkirk deserves recognition.

Owned by Bill Whitbread and trained by Peter Cazalet, Dunkirk is probably best remembered for winning what is now the Queen Mother Champion Chase by 20 lengths in 1965. However, the following season, he also beat Mill House by 15 lengths, at level weights, in the Frogmore Chase at Ascot and won what is now the Paddy Power Gold Cup at Cheltenham under 12st 7lb.

Dunkirk never did beat Arkle, but did, quite literally, die trying. The pair met for the one and only time in the King George VI Chase at Kempton in December, 1966, for which Arkle was sent off 1/7 favourite in a field of four. Despite attempting three miles for the first time, Dunkirk jumped spectacularly at the head of affairs and was, at one stage, nearly a fence clear of his rivals. However, as his stamina waned, he was gradually reeled in by Arkle. At the final open ditch, five fences from home, Dunkirk failed to take off at all, breaking his neck in a fatal fall; he was subsequently found to have suffered a lung haemorrhage.

Harry Whittington, who is based at Hill Barn Stables in Sparsholt Firs, near Wantage, Oxfordshire, overlooking Lambourn, first took out a training licence in 2012. He enjoyed his most successful season, numerically and fiscally, in 2019/20, when he trained 30 winners from 160 runners, at a strike rate of 19%, and amassed over £450,000 in prize money. His biggest payday that season came on March 12, 2020, at the Cheltenham Festival, when Simply The Betts, ridden by Gavin Sheehan, justified favouritism in the Grade 3 Brown Advisory & Merriebelle Stable Plate, worth nearly £62,000 to winning connections.

By that stage of his career, Whittington had long since saddled his one and only Grade 1 winner, Arzal, in the Manifesto Novices’ Chase at Aintree on April 7, 2016. Tragically, Arzal was put down shortly afterwards due to complications arising from a minor leg injury, but the form was franked by the second and third horses, L’Ami Serge and Sizing John, who won the Grande Course de Haies d’Auteuil and the Cheltenham Gold Cup the following year!

In March, 2023, Whittington announced that he would be reliquishing his training licence at the end of the 2022/23 National Hunt season, in favour of a return breaking-in and pre-training young horses, something he had done successfully for the likes of Nicky Henderson and Tom Dascombe before turning his hand to training. He told the Racing Post, ‘I have always loved pre-training horses. It’s something I get a real kick out of, and it was something we have always considered doing again.’ Whittington duly saddled his final runner, Docpickedme, who was pulled up, in a handicap hurdle at Warwick on April 27, 2023. All told, he trained over 180 winners, including a handful on the Flat, which was a fair return for someone who once told ‘Trainer’ magazine, ‘I actually had no aspirations to be a trainer whatsoever.’