Crowe started his career as a trainee at Arsenal, although he was unable to break into the first team, with veteran right back Lee Dixon usually occupying the slot. He made his debut as substitute in a League Cup tie against Birmingham City on 14 October 1997 but was sent off after just 33 seconds by referee Uriah Rennie for a foul on Martin O'Connor. It was the fastest debut sending-off in English football history. That season he also contributed to Arsenal's run in the FA Cup, coming on as a substitute against Crystal Palace in the fifth round. However, he wasn't part of the squad when they won the 1998 FA Cup Final. He played one more match for Arsenal (in the League Cup against Derby County). After a loan spell at Crystal Palace he moved to Portsmouth in July 1999, with Arsène Wenger deeming him surplus to requirements.