Following a successful loan spell with Crewe Alexandra in the 1999–2000 season, Wright made his Liverpool debut in the 8–0 drubbing of Stoke City on 29 November 2000 in the League Cup, replacing Markus Babbel at half time. He went on to play 4 times that season for Liverpool, including a brief substitute appearance against future club Sunderland at the Stadium of Light in February 2001. He was also an unused substitute as Liverpool won the 2001 UEFA Cup Final.