- The annual jockey awards The Lesters, inaugurated in 1990, are named in his honour.
- On Tuesday 15 May 2007 he was admitted to intensive care in a Swiss hospital following a recurrence of a previous heart problem. His wife stated that this illness is not life-threatening and that he was recovering in intensive care as a precaution. He attended Royal Ascot in June 2007 and the Epsom Derby in June 2008 where he tipped the winner, New Approach, during a BBC television interview. He was also present for Gold Cup day at the Cheltenham Festival in March 2009, where he was interviewed in the parade ring.
- Piggott retired as a jockey at the end of the 1985 flat season and became a trainer. At its peak, his Eve Lodge stables housed 97 horses and sent out 34 winners. In 1987 he was convicted of tax fraud and jailed for three years, of which he served 366 days. The following year he was stripped of his OBE (which he had been awarded in 1975) because of his conviction. Once released from jail, he resumed his career as a jockey in 1990 and won the Breeders' Cup Mile on Royal Academy within ten days of his return. He rode another Classic winner, Rodrigo de Triano, in the 1992 2000 Guineas. His last win was in October 1994 and he officially retired, this time for good, in 1995. In 2004 he published the book Lester's Derbys.
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