In Great Britain's National Hunt racing, the title of Champion Jockey is bestowed on the jockey who has ridden the most winning horses during a racing season. Having been runner up to Tony McCoy on 16 occasions in the Champion Jockey title, he was finally crowned champion for the first time in 2016.

Richard became Champion Conditional Jockey in 1995, at the age of 18. The first winner of Richard's riding career was on Rusty Bridge at Hereford in April 1994.

He has had great success at the Cheltenham Festival. His first win at Cheltenham was on Anzum in the 1999 Stayers' Hurdle. He won the 2000 Tote Cheltenham Gold Cup with Looks Like Trouble and the 2002 Queen Mother Champion Chase with Flagship Uberalles. Richard was also victorious in the 2003 Smurfit Kappa Group Champion Hurdle with the Philip Hobbs-trained Rooster Booster on which he also came 2nd in 2004. He is one of only three jockeys riding today, the other beings Barry Geraghty and Ruby Walsh, to have won all four of those championship races at Cheltenham.

In 2003, Richard became the eighth National Hunt jockey to ride 1,000 winners in Britain on Quedex at Stratford. He recorded his 2,000th career winner aboard Fighting Chance at Newbury on 16 December 2009. The 3,000th winner came on board St. Saviour at Ludlow on 4 January 2016.

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