Painter finished his career second to only Drew Brees in Big Ten history in passing attempts (1,648), completions (987) and passing yards (11,163). Painter also ranked third eighth in passing touchdowns (67). After the 2008 season, Painter was invited to participate in the 2009 Texas vs The Nation All-Star Classic, where he was 6-of-15 for 55 yards and a touchdown for the winning Nation team.
Painter made his NFL debut in relief of Peyton Manning in Week 16 of the 2009 season. At the time, the Colts were 14-0 and leading the New York Jets 15-10, but Painter committed two turnovers, leading to the Colts first loss of the season. Painter relieved Manning again the following week, but was unable to lead the Colts to a win. He did not play in either of the Colts two playoff victories leading up to Super Bowl XLIV, nor did he play in the Super Bowl.