He scored on his debut in an emphatic 4-0 win at White Hart Lane versus Watford. Allen went on to play in two FA Cup finals for Tottenham Hotspur, on the losing side in 1987 alongside his cousin Clive Allen. However, Allen was victorious in the 1991 FA Cup defeating Nottingham Forest 2-1. In eight years with Tottenham, he played 292 league games and scored 23 goals. He was voted player of the year for the 1992–93 season, his final full season at White Hart Lane.