Grayson and Leeds started the 2009–10 season with an unbeaten run in all competitions, which included seven victories and a draw in League One and saw the club progress to the third round of the League Cup, before losing 1–0 to Liverpool. In that season's FA Cup, Grayson led Leeds to a 1–0 victory away to Manchester United, their first win at Old Trafford since 1981. Grayson's side also earned Leeds a replay against Premiership opposition Tottenham Hotspur after a 2–2 draw at White Hart Lane.