To date Ruby has ridden over 2000 winners including 52 winners at the Cheltenham Festival since his first win in 1998 on Alexander Banquet. These include the 2004 Queen Mother Champion Chase on Azertyuiop, the 2007 and 2009 Cheltenham Gold Cup on the favourite, Kauto Star and two subsequent Queen Mother successes in 2008 and 2009 on the brilliant Master Minded.
He also won both the 2006 Tingle Creek Chase and the King George VI Chase on Kauto Star. He repeated the King George feat, again on Kauto Star, in 2007, 2008 and 2009 when Kauto Star won impressively by 36 lengths. He reclaimed the King George VI Chase in 2011 on board Kauto Star after Long Run won the race in 2010. He won the Hennessy Gold Cup twice, in 2003 on Strong Flow, and in more recent times, 2009 with Denman. He also won the Whitbread Gold Cup twice, in 2001 and 2003 both times on Ad Hoc.
In 2007, Ruby won the inaugural British Horseracing Board Jockeys’ Order of Merit award.