After starting every game of the 2008 season leading up to the Florida State game on October 25, Taylor suffered a high ankle sprain on the first play of the Florida State game. Sean Glennon relieved Taylor at the quarterback position after this setback. While Glennon got the start versus Miami, Taylor split time with Glennon and led a crucial fourth quarter to make it a two-point game 16–14. However, he was sacked in a crucial 4th and 3 with less than two minutes to go. After the loss, Taylor started against Duke. After committing five turnovers in the first half, he was pulled from the game and replaced by Sean Glennon. Taylor then started next week at Virginia. He performed well including a 73-yard run. He was 12-for-18 for 137 yards and one touchdown while rushing 16 times for 137 yards. He then started in the ACC Championship Game win over Boston College and was named the ACC Championship Game MVP. On January 1, 2009, he led the Hokies to a 20–7 victory over the Cincinnati Bearcats in the 2009 Orange Bowl. Overall, he finished his sophomore season with 1,036 passing yards with two touchdowns and seven interceptions.