A. A. Thomson wrote that Winchilsea "would go anywhere for a game of cricket". He was certainly prolific and is one of the most recorded players of the 18th century, though he was far from being among the best and was already 33 when he was first recorded in a senior match. He is known to have played in more than 130 top-class matches from 1785 to 1804, and records of many other matches have certainly been lost. His level of activity is matched by few of his contemporaries; only Billy Beldham and Tom Walker made a substantially greater number of appearances. Lord Frederick Beauclerk and George Louch were the only amateurs of the time as prolific as Winchilsea, but they were much better players because Winchilsea on the field was something of a liability. His known career batting average was a lowly single figure, despite using a bat that weighed 4 lb 2 oz.