During Tillman's three years with the team they hosted three consecutive home playoff games and played in two Grey Cups. In 2007, the Roughriders won their third ever Grey Cup. Among the key signings made by Tillman were head coach Kent Austin, defensive end Stevie Baggs, receivers Weston Dressler and Rob Bagg, defensive back Omarr Morgan, and running back Corey Holmes. He also acquired many key players who would be part of the Roughriders 2013 championship season, including Darian Durant, Chris Getzlaf, and John Chick. In July 2008, Tillman was given a contract extension through 2010.