Born in Kendal on 24 June, 1732, John Singleton of Westmorland, no relation to other Singletons, was the son of a horse dealer.
He had his first ride at Kirkby Lonsdale when aged 16. He had his last ever ride at Chester in 1784.
He managed to save up some money with which, rather foolishly, he bought a racehorse. Shortly after, he had the mortification of seeing his horse break a leg while running at Burnwood. He then became a horsebreaker and farrier but slowly became reduced in circumstances and, after receiving a weekly allowance of 3 shillings from the Parish Board of Chester, was admitted to the Chester House of Industry (workhouse) where he spent his last five years. He became senile and claimed to have ridden the winner of the first St Leger.