coach Lloyd Carr, Henson battled for the starting quarterback job against Tom Brady and ultimately was named the backup for the 1998 season. He saw action in 8 games, accumulating 21 completions on 47 pass attempts, good for 254 yards, three touchdowns and one interception. He saw action in seven of Michigan's 13 games, including a win over #11 Arkansas in the Citrus Bowl. In 1999, Brady had to once again hold off Henson for the starting job. The two players platooned during the season's first seven games, with Brady playing the first quarter, Henson the second and Carr then deciding upon a quarterback for the second half. The team started off with a 5–0 record. Against Michigan State, Henson in the second quarter connected with Marcus Knight for the third longest passing play in school history (an 81-yard touchdown completion); so he was chosen to play in the second half; however, Brady was reinserted into the game in the fourth quarter with Michigan down by 17 points, and nearly led the team all the way back before losing 34–31. After a 300-yard passing game the following week, Carr went exclusively with Brady for the remainder of the season. Henson still saw his number of pass attempts nearly double, throwing 90 times and completing 47 passes. He recorded 546 passing yards, along with three touchdowns and two interceptions in nine appearances. Henson again saw limited action when Michigan took on another bowl opponent with a higher ranking, #5 Alabama, in the Orange Bowl, and came out victorious with a 35–34 OT victory. In 2000, Brady graduated and Henson, now a junior, served as the Wolverines' starting quarterback for most of the season. He missed the first 3 contests after having surgery on his right foot just prior to the start of the season on August 24, with redshirt freshman John Navarre replacing him. Henson threw for a career-high 312 yards in a road loss to #21 Northwestern, 54–51, and also tied a school record with four passing touchdowns. In the regular season finale, Henson led the #19 Wolverines to Columbus to take on #12 Ohio State and threw again for over 300 yards en route to a 38–26 win. For the third time in his career, Michigan and Henson faced a Southeastern Conference team when Michigan went on to play Auburn in the Citrus Bowl and for the third time,