The 1998 – 1999 campaign proved to be a fine one for Martin O’Neill’s’ Leicester City side as Emile Heskey and Ian Marshall was outstanding for the club and Robbie Savage was beginning to develop in to a great premiership player. The 1998 – 1999 season saw the foxes reach the final of the league cup (Worthington Cup); however they suffered defeat in the final, losing against Tottenham Hotspur. The 1999 – 2000 campaign proved to be a great one for Leicester City fans as the club once again reached the finals of the league cup, this time defeating Tranmere Rovers in the final of the competition to win it for the second time in four years.
Martin O’Neill left the club for Glasgow Celtic at the end of the season and Peter Taylor took charge at the club. Leicester city were top of the premiership in November 2000 as Taylor and Steve Walsh was named as premiership manager and player of the month respectively. After bad run at the end of the season they finished it off in 13th position. They reached the quarter finals of the FA cup, suffering defeat against Wycombe Wanderers in the last eight.