Gill signed a two-and-a-half-year contract in January 2001. Having taken part in most of the games in Birmingham's League Cup run, he was omitted from the first leg of the semi-final at Ipswich Town in favour of loan player Steve Jenkins. When Jenkins returned to his owning club, Gary Rowett said that Gill should be given a run of games in the Birmingham first team, suggesting that "if anything, he's too nice. He doesn't complain a lot and it's easy for people not to take notice of you. Perhaps if he moaned a bit more he'd get a start!" Recalled for the second leg, he produced an excellent performance, making a goal-line clearance from a header which would have left Birmingham two goals adrift had it crossed the line. Yet when it came to the final, manager Francis was unable to find a place for Gill even among the substitutes, preferring Eaden and McCarthy, making only his second start after recovering from a broken leg, in the starting eleven and David Holdsworth, a defender unavailable since the previous November due to serious illness, on the bench. Gill was devastated by this decision, describing it as "the biggest disappointment of [his] whole life".