Tyson began his career at Reading as part of the youth academy, and made his first team debut on 29 April 2000, coming on as an 80th-minute substitute for Darius Henderson in a 1–1 draw with Bury at Gigg Lane. In August 2001, he joined Swansea City of the Third Division on an initial one-month loan. On 29 September, he was sent off for a foul on goalkeeper Stuart Brock two minutes after coming on as a substitute in a 2–0 win over Kidderminster Harriers at Aggborough, though manager Colin Addison said that he intended to appeal the decision as Tyson was "only a fraction from taking the ball". Tyson scored his first goal in the Football League on 23 October, helping the "Swans" to a 2–0 win over Darlington at Vetch Field. He returned to the Third Division towards the end of the 2001–02 season, joining Cheltenham Town on loan in March 2002. Manager Steve Cotterill signed him to help the club push for the play-offs, and Tyson scored one goal from one start and seven substitute appearances in the league, but did not feature in the play-offs as the "Robins" went on to secure promotion with a 3–1 victory over Rushden & Diamonds in the play-off final.
