Di Santo came on as a substitute for Florent Malouda with half an hour remaining and Chelsea a goal down against Stoke City on 17 January 2009. He assisted a goal in the 88th minute for Juliano Belletti to make it 1–1, and Frank Lampard then scored a 94th-minute winner. On 30 May, Di Santo was an unused substitute as Chelsea won the 2009 FA Cup Final against Everton. He made 8 substitute appearances during Chelsea's 2008–09 Premier League campaign and was afterwards linked with a loan move to Blackburn Rovers.