He established himself as a key first team player under Dave Bassett and was named as the club's Player of the Year in the 1999–2000 season, playing a total of 45 games, including three appearances in the play-offs as Barnsley reached the play-off final at Wembley, where they lost 4–2 to Ipswich Town. He also scored his first goal in professional football in a 3–2 League Cup victory over Bradford City at Valley Parade on 12 October. He made 45 appearances in the 2000–01 season, and scored the only goal of the game against Burnley in caretaker-manager Eric Winstanley's first game in charge on Boxing day. He was also sent off twice, firstly for a bad foul on Birmingham City's David Holdsworth in a 4–1 defeat at St Andrew's on 28 August and secondly for a professional foul on Ian Moore in a 2–1 defeat to Burnley at Turf Moor on 20 January. Late in 2000 he was also linked with a move to Bobby Robson's Newcastle United however this never materialised.