 He joined Havant & Waterlooville on loan in August 1999, playing in the first eight league games of Havants' first season in the Southern League Premier Division.He also had a spell on loan with Newport (Isle of Wight) from March to May 2000 and finally made his Portsmouth debut in their 2–1 defeat at home to Tranmere in the FA Cup on 6 January 2001.He made four further appearances for Portsmouth that season, all in the Championship as Portsmouth successfully avoided relegation.