[citation needed] The 6ft5 small forward began his pro career in 1994 when he signed for the London Towers, after attending Georgia Southern University.
The 1995–96 season saw the beginning of the trophy spree, when Windless helped the Towers to a 70–58 National Cup final victory against the Sheffield Sharks, on their own turf.
The following season, which saw another him elected to another All-Star game appearance, Tony helped Towers to another Trophy win and a victorious Playoff run, beating fierce rivals Greater London Leopards 89–88 in an intense Wembley final.
While in Newcastle, he regained his impeccable form from the Towers days, leading the previously fledgling franchise to a Trophy final, in which they finished runners-up to the victorious Chester Jets, 92–81.
After starring in the French leagues for Montpellier, Gravelines and Besançon, Windless returned to the UK in 2004 to play for Scottish Rocks.