How many times has Tiger Roll won at the Cheltenham Festival?

Of course, Tiger Roll is best known for becoming the first horse since Red Rum, in 1974, to win back-to-back renewals of the Grand National. However, since his second win in the world famous steeplechase, in 2019, his name has become associated with some ludicrous, frankly reprehensible, remarks by his owner, Michael O’Leary. O’Leary’s disgraceful, ‘holier than thou’ attitude has been well chronicled elsewhere, but should not be allowed to overshadow Tiger Roll’s achievements.

The Grand National aside, Tiger Roll has been a fine servant to connections at the Cheltenham Festival. He was originally bought by Gigginstown House Stud with a view to winning the Fred Winter Juvenile Novices’ Handicap Hurdle, but exceeded expectations; on just his third run over hurdles, he not only contested, but won, the Grade 1 Triumph Hurdle at the 2014 Cheltenham Festival.

Tiger Roll returned to the Cheltenham Festival in 2015, finishing down the field, at 50/1, in the Stayers’ Hurdle. However, slightly surprisingly, given his diminutive stature, fences proved to be the making of him. He won the National Hunt Chase at the 2017 Cheltenham Festival, followed by the Glenfarclas Chase, on the idiosyncratic Cross Country Course, in 2018, 2019, and 2021. Tiger Roll currently has five Cheltenham Festival victories to his name and, amidst the hoo-ha surrounding his non-participation in the Grand National, O’Leary has confirmed that he will attempt a sixth, in the Glenfarclas Chase again, in 2022 before being retired.

Has a female jockey ever won the Cheltenham Gold Cup?

Has a female jockey ever won the Cheltenham Gold Cup?  The simple answer is no, not yet, but until recently female jockeys in the Cheltenham Gold Cup had been few and far between. In fact, the first female jockey to ride in the ‘Blue Riband’ event was the late Linda Griffiths, formerly Sheedy, who failed to complete the course on 500/1 rank outsider Foxbury in 1984. Remarkably, the second was not until 2017, when the now-retired Lizzie Kelly was unseated at the second fence by Tea For Two, although the partnership did return to Cheltenham to finish a distant seventh in 2018.

More recently, the redoubtable Rachael Blackmore has gone closest to becoming the first female jockey to win the Cheltenham Gold Cup. In 2020, she rode Monalee, trained by Henry De Bromhead, to finish fourth, beaten just 1¾ lengths, behind Al Boum Photo. In 2021, having already won the Champion Hurdle on Honeysuckle, for the same trainer, she rode A Plus Tard to finish second, beaten 1¼ lengths, behind stable companion Minella Indo in the Cheltenham Gold Cup. In that same race, Bryony Frost also rode Frodon to finish fifth, albeit 33¾ lengths behind the winner.

How many female trainers have won the Cheltenham Gold Cup?

How many female trainers have won the Cheltenham Gold Cup?  The short answer is three, although those three female trainers are actually responsible for six Cheltenham Gold Cup victories between them. Jenny Pitman, who had already made history by becoming the first woman to saddle a Grand National winner in 1983, wasted no time when repeating the dose in the Cheltenham Gold Cup in 1984, courtesy of Burrough Hill Lad. She also won the ‘Blue Riband’ event again in 1991, with Garrison Savannah, ridden by her son, Mark.

Just over a decade later, in the wake of an outbreak of foot-and-mouth disease, which caused the 2001 Cheltenham Festival to be abandoned, Henrietta Knight saddled Best Mate to a notable hat-trick in the Cheltenham Gold Cup in 2002, 2003 and 2004. He became the first horse since the legendary Arkle, 38 years earlier, to win the race three years running.

Last, but by no means least, Irish trainer Jessica Harrington saddled Sizing John to win the Cheltenham Gold Cup in 2017. Mrs. Harrington, 70, was having her first runner in the race and later joked about ‘beginner’s luck’, despite having previously won the Queen Mother Champion Chase (twice) and the Champion Hurdle.

Before First Flow, what was Kim Bailey’s last Grade One winner?

After he had given 17lb and upwards away to his rivals when recording a game, albeit narrow, victory, on heavy going, in the Castleford Handicap Chase at Wetherby in December, 2020, Kim Bailey described First Flow, who was completing a five-timer, as an ‘extraordinary horse’. However, the Andoversford trainer had further cause for celebration the following month, when the 9-year-old belied odds of 14/1 to win the Grade One Clarence House Chase at Ascot and, in so doing, beat the reigning two-mile champion chaser, Politologue, by 7 lengths at level weights.

Victory in the Clarence House Chase was also notable for the fact that it was the first time in 9,443 days, or 25 years, 10 months and 5 days, that Bailey had saddled a Grade One winner. Remarkably, his last winner at the highest level was Master Oats, ridden by the long-retired Norman Williamson, in the Cheltenham Gold Cup in 1995! To be fair, having won the Champion Hurdle 48 hours earlier with Alderbrook, Bailey was completing the Champion Hurdle – Cheltenham Gold Cup double, making him the last trainer to do so. Nevertheless, fans of nostalgia might like to know that, at the time, John Major was Prime Minister, a pint of lager cost £1.66 and ‘rogue trader’ Nick Leeson had just caused the collapse of Barings Bank.

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