In his sophomore season, Freeman threw for 3,353 yards, a Kansas State record. He also broke school records for completions, attempts, and 300-yard games in a season. As a junior, he racked up 20 TD passes and only threw eight interceptions, while also rushing for 14 TD. Freeman finished his Wildcats career as the school record holder for completions, attempts, yards, touchdowns, and total offense, but his career record as a starter was only 14-18.
Freeman made his NFL debut in mop-up duty in the Buccaneers Week 7 loss to the Patriots in London. He was named the starter for their next game, in Week 9. In his first career start, Freeman threw for 205 yards and 3 touchdowns to lead the Buccaneers to their first win of the season. Freeman finished the 2009 season with 1,857 passing yards, 10 touchdowns and 18 interceptions. He was 3-5 as the starting quarterback.