 Kitson began his career as a trainee at Leicester City in 1988.In one season at Leicester, Kitson and Ian Baraclough, his striking partner, scored 60 or so goals between them for the youth and reserve sides.Baraclough was sold to Grimsby Town, while Kitson scored 11 goals in 63 appearances for the Leicester first-team, and joined Derby County for a club record of £1.3 million transfer fee in March 1992, made up of £800,000 with Phil Gee and Ian Ormondroyd moving to Leicester in part exchange.