At Leicester, Whitlow became a first-team regular and was a member of the side that won the 1997 League Cup. In total, he played 180 games for the Foxes and scored nine goals. He then moved on to Bolton Wanderers in September 1997 for a £500,000 fee. At Bolton, Whitlow is remembered for being sent off in the dramatic 2000 playoff semi-final against Ipswich Town that Ipswich went on to win 5-3 after extra time, following a Jim Magilton equaliser in the last minute of normal time. The following season, Whitlow missed most of the action because of injury, but he returned to the side just in time for the playoffs, where Bolton this time got promoted to the Premier League.