He scored two goals in 39 appearances throughout the 1998–99 season, helping Martin O'Neill's "Foxes" to a 10th-place finish. Six of his appearances came in the League Cup, though he was not in the matchday squad for the final, a 1–0 defeat to Tottenham Hotspur. He appeared 44 times in the 1999–2000 campaign and this time was part of the team that played in the League Cup final, and collected his second winners medal in the competition as Leicester triumphed 2–1 over Tranmere Rovers thanks to a brace from centre-back partner Matt Elliott.