In the past decade at the Cheltenham Festival, while the Irish Independent 
Leading Trainer Award has been presented to just four men, the Holland 
Cooper Leading Jockey Award has been presented to just three, Ruby 
Walsh, Barry Geraghty and, most recently, Davy Russell.
Thanks in large part to long, fruitful associations with Paul 
Nicholls and Willie Mullins – multiple champion trainers on their 
respective sides of the Irish Sea – Ruby Walsh is, far and away, the 
most successful jockey in the history of the Cheltenham Festival. 
Coincidentally, Walsh has ridden 58 winners, exactly the same number as 
Geraghty (36) and Russell (22) put together, which may account for the 
fact that he has won the Holland Cooper Leading Jockey Award eight times
 in the last ten years – and eleven times in all – whereas Geraghty and 
Russell have won it just once apiece.
Nevertheless, just over two decades ago, on the eve of the Cheltenham
 Festival in 1998, none of these leading jockeys had ridden a single 
winner at the so-called ‘Olympics of Horse Racing’, so it’s interesting 
to know how, and when, they began their quest for stardom.
Unsurprisingly, Ruby Walsh was the first to open his account at the 
Festival, when still an 18-year-old amateur, in 1998. That said, ‘Mr. R.
 Walsh’, as he was known to racegoers at the time, was reigning Irish 
amateur champion and rewarded the faith shown in him by Willie Mullins 
by guiding the five-year-old Alexander Banquet to a 2½-length victory of
 the favourite, Joe Mac, in the Weatherbys Champion Bumper.
Barry Geraghty broke his duck at the Cheltenham Festival, at the age 
of 23, in 2002, partnering Moscow Flyer – who would later be rated 
alongside Burrough Hill Lad and Long Run in the top ten steeplechasers 
of the Timeform era – to a ready, 4-length win over the favourite, 
Seebald, in the Arkle Challenge Trophy. Now the fourth most successful 
jockey in the history of British National Hunt racing, and retained by 
powerful owner J.P. McManus, he still has time to increase his winning 
tally at the Festival.
Davy Russell, at the age of 39, is roughly the same age as Walsh and 
Geraghty, but was a relative latecomer to Festival success, partnering 
his first winner, Native Jack, in the Cross Country Chase in 2006. Even 
so, he has enjoyed a steady stream of winners – at least one at every 
Cheltenham Festival – ever since, including winning the Cheltenham Gold 
Cup on Lord Windermere in 2014. In fact, Russell enjoyed his best 
Cheltenham Festival ever, numerically, with four winners, including 
Balko Des Flos in the Ryanair Chase to win the Holland Cooper Leading 
Jockey Award  for the first time.
With International Women's Day just gone, let's not forget the 
contributions of female jockeys to the Cheltenham Festival. Nina Carberry rode her first winner at the Cheltenham Festival, Dabiroun, in the Fred Winter Juvenile Novices’ Handicap Hurdle in 2005 and subsequently rode six more winners to become the most successful female jockey in the history of the Festival. Historically female jockey participation at Cheltenham has been a rarity especially when compared to the Grand National. That's changing though, with a record breaking four wins for female jockeys at the 2018 Cheltenham Festival including Lizzie Kelly on Coo Star Sivola in the Ultima Handicap Chase. 
Kelly will be back on the same horse in the 2019 Festival, in addition to two other rides. Other female jockeys such as Rachael Blackmore and Bryony Frost will feature too to the potential for another bumper year for the ladies is high!
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