In August 2005, Long suffered an ankle injury and was sidelined as the 2005 Michigan Wolverines football team's season began. The injury had been caused in training camp when he was zone blocking alongside center Mark Bihl, who got tangled up with nose tackle Gabe Watson. The two fell against the outside of Long's leg and rolled over it. The injury required surgery. Long did not return to the lineup until October 22 on the third possession against the Iowa Hawkeyes. He was the lead blocker on the game-winning overtime touchdown. He started the game the subsequent week against the Northwestern Wildcats. Two weeks later, following a bye week, Long got injured during the first half against the Indiana Hoosiers, and his foot was put in a protective boot. The second foot injury was expected to end his season. He appeared in the subsequent rivalry game against the Ohio State Buckeyes, and during the first play, he opposed Bobby Carpenter and Carpenter got a broken leg. After the game, Long appeared to need immediate surgery, which would have caused him to miss the 2005 Alamo Bowl. By the time of the game on December 28, though, he was ready to play. As the team prepared for 2006 spring practice, the left-handed Long was moved from right tackle to left tackle where he would be protecting the blindside of right-handed quarterbacks.