Crosby signed with Alan Murray's Darlington in December 1993, which went on to end the 1993–94 campaign second-from-bottom of the Football League. Darlington also finished second-from-bottom in 1994–95, with Crosby clocking up 41 appearances. The "Quakers" improved under new manager Jim Platt, and Crosby played 55 games in the 1995–96 campaign as Darlington qualified for the play-offs after finishing in fifth-place; he played in a back five alongside centre-backs Sean Gregan and Matty Appleby, supported by wing-backs Mark Barnard and Simon Shaw. He captained the club in their play-off final defeat to Plymouth Argyle, the club's first appearance at Wembley Stadium."Mauge magic". The Sunday Mirror. London. 26 May 1996. Retrieved 10 March 2010. However Darlington returned to the lower half of the division under new manager David Hodgson, finishing 18th in 1996–97 and 19th in 1997–98, with Crosby bringing his final tally at Darlington to 211 league and cup appearances.
