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The 1999 Cheltenham Festival marked the arrival at the ‘top table’ of British trainers of Paul Nicholls, who, at the time of writing, has since won the National Hunt Trainers’ Championship 14 times, just one shy of the record set by Martin Pipe in 2004/5. That year, Nicholls won the first of his six leading trainer awards at the Cheltenham Festival with three winners, namely Flagship Uberalles in the Arkle Challenge Trophy, Call Equiname in the Queen Mother Champion Chase and, most notably, See More Business in the Cheltenham Gold Cup.

On good to soft going, 12 horses went to post in the Gold Cup, with Florida Pearl, trained by Willie Mullins, sent off 5/2 favourite after a comfortable, 2-length win in the Hennessy Cognac Gold Cup at Leopardstown the previous month. In fact, the Florida Son gelding was seeking a Cheltenham Festival hat-trick after winning the Weatherbys Champion Bumper in 1997 and the Royal & Sunalliance Chase in 1998, but while he challenged, going well, three from home, he was beaten from the final fence and eventually finished third, beaten 18 lengths.

See More Business, meanwhile, was involved in a ding-dong battle with one of the rank outsiders, Go Ballistic, over the final two fences. At the final fence, the pair were in the air together and Nicholls’ charge, himself a 16/1 chance, found just enough under Mick Fitzgerald to get the better of Go Ballistic, ridden by Tony Dobbin, and win, all out, by a length. In a classic understatement, Fitzgerald later told the BBC, “All I have done is the steering, really.” At the time of his death in 2014, aged 24, Nicholls said of See More Business, ” He was a fantastic horse. The horse of a lifetime.”

Seventeen horses went to post for the 1998 Cheltenham Gold Cup, including the second, third and fourth from the previous year, Barton Bank, Dorans Pride and Go Ballistic. Dorans Pride had won five of his six starts since, including an easy, 15-length victory in the Henessy Cognac Gold Cup at Leopardstown on his most recent outing. He was sent off favourite, at 9/4, ahead of the King Geoge VI Chase winner, See More Business, at 11/2, with Suny Bay at 9/1 amd 10/1 bar the front three.

In a bizarre incident approaching the seventh fence, Tony McCoy pulled up his mount, Cyborgo, who had gone lame, but, in doing so, carried out both See More Business and ramk outsider Indian Tracker. Meanwhile, former hunter chaser Cool Dawn, trained by Robert Alner and ridden by Andrew Thornton, continued to make the running, as he had done from flagfall. In fact, making just his second appearance at Grade 1 level, the 10-year-old was never headed. He had to be hard ridden on the run-in, but nonetheless ran on well to beat his nearest pursuer, Strong Promise, by 1¾ lengths, with Dorans Pride, who had been outpaced after making a mistake at the third-last, staying on well for third place, just a head further behind.

Cool Dawn was returned at 25/1 and never hit the same heights again, being pulled up on three of his final four starts, including when favourite for Whitbread Gold Cup at Sandown the month after his Cheltenham triumph. At the time of his death in 2018, aged 30, Thornton reflected on his victory, saying, “He [Cool Dawn] absolutely flew five out for me and every fence from there. His jumping won it.”

The 1997 Cheltenham Gold Cup once again featured Imperial Call, Barton Bank and One Man, first, fourth and sixth in the 1996 renewal, plus Dublin Flyer, who failed to finish on that occasion. Defending champion Imperial Call had fallen in the Punchestown Chase, with the race at his mercy, on his reappearance in December and finished a distant third, when favourite, in the Hennessy Cognac Gold Cup at Leopardstown in February. He was again sent off favourite for the Cheltenham Gold Cup, but ran a lifeless race and was tailed off when pulled up five fences from home. One Man, who had weakened so dramatically in the closing stages in 1996, did so again and, once again, finished a tired sixth.

Mr. Mulligan, trained by Noel Chance, had fallen at the final fence, when beaten, in the King George VI Chase at Kempton when ridden for the first time by Tony McCoy, but the partnership proved a different proposition at Cheltenham. Belying odds of 20/1, the nine-year-old led heading down the back straight for the final time, went clear at the third-last fence and, despite edging right on the run-in, was driven out to win by 9 lengths. Barton Bank stayed on for second, with Dorans Pride a further half a length back in third place.

Mr. Mulligan became a first Cheltenham Gold Cup winner for McCoy and, in so doing, completed a notable double for the Northern Irishman, who had won the Champion Hurdle on Take A Stand, trained by Martin Pipe, two days earlier. McCoy later said of Mr. Mulligan, “When I gave him a little smack, he warmed up and I knew when I let him stride on that he was warming to his task.”

At the time of writing, nine of the last 10 renewals of the Cheltenham Gold Cup, including the last seven in a row, have been won by horses trained in Ireland. However, believe it or not, there was a time, not so long ago, when the concept of an Irish ‘drought’ in the steeplechasing showpiece was a real possibility. Indeed, such a paucity of Irish-trained winners had existed for the decade prior to the 1996 Cheltenham Gold Cup.

Nevertheless, that all changed on March 14, 1996, when Imperial Call, trained by Fergus ‘Fergie’ Sutherland in Co. Cork and ridden by Conor O’Dwyer, saw off the British-trained hotpot, One Man, and eight other rivals to win the ‘Blue Riband’ event. Trained by Gordon Richards in Cumbria, One Man was sent off 11/8 favourite to follow up his easy, 14-length win in the rearranged King George VI at Sandown Park in January, but stopped as if shot approaching the final fence and eventually trailed in a tired sixth of the seven finishers.

Imperial Call, though, took over from the weakening Couldnt Be Better at the fourth-last fence and, thereafter, never really looked in danger of defeat. Indeed, Sutherland said later, “In the last mile, I must confess I had a feeling of inevitability about it. I just knew he was going to win.” Rough Quest, trained by Terry Casey and ridden, stealthily, by Mick Fitzgerald, chased the winner from two out, but could only find one pace in the closing stages and eventually finished second, beaten 4 lengths. The first two pulled 19 lengths clear of the third horse home, Couldnt Be Better.

Run on soft going, the 1995 Cheltenham Gold Cup featured 15 runners, including the second, third and fourth from the 1994 renewal, Jodami, Young Hustler and Flashing Steel. Victory, though, went to the favourite, Master Oats, trained by Kim Bailey and ridden by Norman Williamson, who was not entirely foot perfect at his fences, but was, nevertheless, ridden clear approaching the final fence and stayed on strongly to win by 15 lengths. Dubacilla, trained by David Nicholson and ridden by Dean Gallagher finished second, a similar distance ahead of the 1994 Grand National winner Miinnehoma, trained by Martin Pipe and ridden by Richard Dunwoody.

Master Oats became the first winning favourite since Desert Orchid in 1989 and his winning margin was the widest since Alveston beat Royal Mail by 25 lengths in 1979. Moreover, he completed a rare Champion Hurdle – Cheltenham Gold Cup double for Bailey and Williamson who, two days earlier, had teamed up to win the two-mile hurdling championship with the former high-class Flat performer Alderbrook, who was having just his second start for the yard. In fact, the last trainer and jockey to achieve the feat were Vincent O’Brien and Aubrey Brabazon who, in 1950, won the Champion Hurdle with Hatton’s Grace and the Cheltenham Gold Cup with Cottage Rake, both of whom started favourite.

Reflecting on his finest hour at Prestbury Park some years later, Bailey said, “Alderbrook was my first Cheltenham winner and you never forget the first and last of anything you do.” However, he was affectionately ambivalent towards Master Oats, saying, “He would run through a brick wall for you and he was not a good jumper; his brain wasn’t quite quick enough for his feet.”