 Brady was a Football Conference champion with Rushden & Diamonds in 2000–01, scoring the winner at his future club Chester City on the final day of the season to make promotion mathematically certain.The following season saw him appear on the losing side for Rushden against Cheltenham Town in the Football League Division Three play-off final at the Millennium Stadium.He also suffered play-off disappointment in the Football Conference with Chester City (2003) and Stevenage Borough (2005).