Notre Dame On September 4, Michigan defeated Notre Dame, 26–22, before a crowd of 111,523 at
Michigan Stadium. Michigan took a 6–0 lead in the first quarter on two field goals by Jeff Del Verne, capping drives of 54 and 38 yards. The second field goal was set up by a Notre Dame fumble at the Michigan 44-yard line. Early in the second quarter, Notre Dame took a 7–6 lead on four-yard run by Joey Getherall. Michigan retook the lead with a 59-yard drive led by
Drew Henson and capped by another field goal from Del Verne. The Fighting Irish then scored on a 12-yard touchdown run by quarterback
Jarious Jackson with 51 seconds remaining in the first half. Notre Dame led, 14–9, at halftime. At the start of the third quarter,
Tom Brady led Michigan on an 80-yard touchdown drive, ending with a two-yard touchdown run by
Anthony Thomas. Michigan added a fourth Del Verne field goal late in the third quarter and led, 19–14, at the end of three quarters. Late in the fourth quarter, Jackson led Notre Dame on a 65-yard drive ending with a 20-yard pass from Jackson to a wide open
Jabari Holloway, on fourth-and-inches and with 4:08 remaining. The Irish then converted a two-point conversion on a pass from Jackson to Bobby Brown. With the clock running down, Michigan drove 58 yards on seven plays, aided by two key penalties against Notre Dame—one for excessive celebration after Holloway's touchdown and a late hit penalty. Michigan scored the winning touchdown on a one-yard run by Anthony Thomas with 1:38 remaining on the clock.In the final minute-and-a-half, Jackson led the Irish to Michigan's 12-yard line before time expired. The game continued the quarterback competition between fifth-year senior
Tom Brady and sophomore
Drew Henson. Brady completed 17 of 24 passes for 197 yards, and Henson completed three of eight passes for 40 yards. Anthony Thomas rushed for 138 yards and two touchdowns on 32 carries. David Terrell caught eight passes for 115 yards. After the game, head coach Lloyd Carr said, "I like them both." Kicker Jeff Del Verne, a walk-on from
Sylvania, Ohio. was granted a scholarship after his 15-point performance against Notre Dame.
Rice On September 11, Michigan defeated Rice, 37–3, before a crowd of 110,501 at Michigan Stadium.
Tom Brady led Michigan on a 58-yard drive late in the first quarter, ending with a 24-yard field goal by Jeff Del Verne. In the second quarter,
Drew Henson led the Wolverines on a 64-yard drive, starting with a 34-yard pass to David Terrell and ending with Henson sneaking across for the touchdown from the one-yard line. At the end of the second quarter, Henson led Michigan on a 53-yard scoring drive ending with a 14-yard touchdown pass from Henson to Terrell. Michigan led, 20–0, at halftime. The Wolverines extended their lead in the third quarter on a pair of touchdown runs by Anthony Thomas. Thomas' first touchdown, an 11-yard run, was set up by Josh Williams' recovery of a Rice fumble at the Rice 46-yard line. The second touchdown, a four-yard run, was set up by Marquise Walker's block of a Rice punt, recovered and returned by Brandon Williams to the Rice four-yard line. The teams traded field goals in the fourth quarter, Rice finally scoring with 30 seconds remaining in the game. Michigan's defense held Rice to 157 yards of total offense and did not allow the Owls to cross midfield until the fourth quarter. Quarterbacks Brady and Henson both played well with Brady playing most of the first and third quarters and Henson the entire second quarter and most of the fourth quarter. Brady completed 10 of 15 passes for 59 yards, and Henson completed eight of 14 passes for 109 yards and a touchdown. The team scored 20 points under Henson and 17 points under Brady. Third-string quarterback Jason Kapsner finished the game for Michigan.
Syracuse On September 18, Michigan defeated Syracuse, 18–13, at the
Carrier Dome in
Syracuse, New York. Syracuse had defeated Michigan one year earlier in Ann Arbor. Neither team scored in the first quarter, as Syracuse was held to minus-17 yards and Michigan had a field goal attempt blocked.
Drew Henson played well in the second quarter, completing nine of 14 passes for 117 yards, including a 22-yard touchdown pass to
Aaron Shea. Jeff Del Verne added two field goals in the second quarter, and Michigan led, 13–7, at halftime. Michigan's offense sputtered in the second half as the Wolverines were limited to 64 yards of offense. Michigan's only offensive points in the second half came on a 31-yard field goal by Jeff Del Verne late in the fourth quarter. Michigan also registered two points on a safety in the third quarter when Syracuse quarterback Troy Nunes was penalized for
intentional grounding in the end zone. In the closing minutes, quarterback Madei Williams led a Syracuse drive to the Michigan eight-yard line. On fourth and four, Williams threw to Pat Woodcock in the end zone; the pass fell incomplete, though replays appeared to show that Michigan defensive back James Whitley had committed
pass interference on the play. The penalty was not called, and Michigan took over on downs with two minutes remaining and was able to run out the clock. The quarterback competition between Brady and Henson remained a focus of the press. Henson played three quarters in the game, completing 16 of 28 passes for 151 yards, one touchdown, and one interception (the first turnover of the season by Michigan). After the game, Henson commented on the extended playing time: "It's the position I've wanted to be in for years. I got my chance tonight." Brady added: "There's certainly no bitterness or jealousy. . . . We continue to compete. We thrive on one another. That's the way it works."
Wisconsin On September 25, Michigan defeated Wisconsin, 21–16, before a crowd of 79,037 at
Camp Randall Stadium in
Madison, Wisconsin. Michigan dominated the first quarter, holding Wisconsin scoreless while
Tom Brady led Michigan on two scoring drives. Michigan's first scoring drive ended with an eight-yard touchdown pass from Brady to Aaron Shea. After
Ron Dayne fumbled, Michigan recovered the loose ball at the Wisconsin 45-yard line.
Davide Terrell the ran 45 yards for the touchdown on a
double reverse. Wisconsin took over in the second quarter with a 32-yard field goal and a 34-yard touchdown run by Dayne. Michigan blocked the extra point kick and led, 14–9, at halftime.
Purdue On October 2, Michigan defeated Purdue, 38–12, before a crowd of 111,468 at Michigan Stadium. In the first quarter,
Tom Brady completed nine of 14 passes for 132 yards and two touchdowns – an 18-yard strike to
David Terrell and a 17-yarder to
Marcus Knight.
Drew Henson took over at quarterback in the second quarter and led Michigan 63 yards on his first drive, ending with a one-yard touchdown run by
Anthony Thomas. Late in the second quarter, Thomas fumbled, and Purdue recovered deep in Michigan territory. Michigan's defense held, and Purdue settled for another field goal by Dorsch with 21 seconds remaining in the half. Michigan totaled 272 yards in the first half and led, 21–6, at halftime. Midway through the second quarter, Purdue scored its only touchdown of the game, as Brees connected with
Vinny Sutherland for a 66-yard touchdown. After the long strike by Brees, Michigan's defense shut down Purdue's offense, and Michigan added to its lead with touchdown runs by Thomas and
B. J. Askew and a 24-yard field goal by Jeff Del Verne. The game featured a quarterback matchup between Brees, considered a leading candidate for the
Heisman Trophy, and Brady, still fighting to keep his job as Michigan's starting quarterback. Brees completed 20 of 49 passes for 293 yards with one touchdown and one interception. Brady completed 15 of 25 passes for 250 yards and two touchdowns. After the game,
The Michigan Daily ran a headline, "Drew who? Brady shows up Brees".
David Terrell played on both offense as a wide receiver and on defense as a defensive back. Thomas rushed for 116 yards and two touchdowns on 23 carries.
Michigan State Illinois On October 23, Michigan lost to Illinois, 35–29, before a crowd of 110,188 at Michigan Stadium. Michigan led, 27–7, late in the third quarter, but Illinois scored 28 unanswered points in the last 18 minutes of the game, including 21 points in the last six-and-a-half minutes. After the game, coach Carr said, "We played as poorly defensively as you can play and suffered the consequences. We're certainly anything but good."
Northwestern On November 6, Michigan defeated Northwestern, 37–3, before a crowd of 110,794 at Michigan Stadium. Michigan dominated the first half, taking a 27–0 lead at halftime.
Tom Brady completed 12 of 23 passes for 185 yards and three touchdowns by
David Terrell for 26 yards in the first quarter,
Marcus Knight for 45 yards in the second quarter, and
Bennie Joppru for 11 yards in the third quarter.
Anthony Thomas also rushed for 172 yards on 17 carries and two touchdowns, including a 60-yard touchdown run in the second quarter. On defense, the Wolverines held the Wildcats to 200 yards of total offense. Terrell also had an interception while playing on defense.
Penn State Ohio State On November 20, 1999, Michigan defeated Ohio State, 24–17, before a crowd of 111,575 at Michigan Stadium. Prior to the game, Ohio State was unranked with a 6–5 record, and Michigan was ranked No. 10 with an 8–2 record. The Buckeyes took a 7–0 lead in the first quarter on a six-yard touchdown pass from
Steve Bellisari to
Kevin Houser. Michigan tied the game in the second quarter on a one-yard touchdown run by
Anthony Thomas. The Buckeyes then retook the lead on a one-yard touchdown run by Jamar Martin and led, 14–7, at halftime. After halftime, the teams traded field goals, and Michigan then tied the game at 17–17 with 37 seconds remaining in the third quarter on an eight-yard touchdown pass from
Tom Brady to Shawn Thompson. With five minutes remaining in the game, Michigan scored the game-winning touchdown on a 10-yard pass from Brady to
Marquise Walker. On January 1, 2000, Michigan defeated Alabama in overtime by a 35–34 score in the
2000 Orange Bowl at
Miami Gardens, Florida. It was the first overtime game in Michigan football history. Neither team had a first down in the first four drives of the game. Michigan finally converted a first down on a fake punt late in the first quarter, but the first quarter ended in a scoreless tie. On its first possession of the second quarter, Alabama drove 76 yards behind long runs by All-American running back
Shaun Alexander. Alexander scored the game's first touchdown on a five-yard run. Alabama's second possession started at Michigan's 31-yard line following a long punt return by
Freddie Milons and a late hit penalty against Michigan. Alexander scored on a six-yard run, and Alabama led, 14–0. With 2:35 remaining in the half,
Tom Brady led Michigan on a 45-yard touchdown drive ending with a 27-yard pass from Brady to
David Terrell with 54 seconds remaining. Michigan's comeback continued on its opening drive of the second half. Brady connected with Terrell for a 57-yard touchdown pass, and the game was tied at 14–14. Alabama then responded as Alexander broke multiple tackles and scored on a 50-yard run through the middle of the Michigan defense. After a three-and-out, Michigan was forced to punt, and Milons scored on a 62-yard return. Alabama again led by 14 points midway through the third quarter. Trailing by 14 points for the second time in the game, Brady led Michigan on a 72-yard drive ending with a 20-yard touchdown pass from Brady to Terrell. It was the third touchdown pass of the game from Brady to Terrell. Michigan drove down the field again on its next possession,
Anthony Thomas scoring on a three-yard run with 1:01 remaining in the third quarter. The game was then tied at 28–28. Michigan drove to the two-yard line early in the fourth quarter, but Thomas fumbled at the goal-line and Alabama recovered the loose ball in the end zone. As time ran out, Alabama blocked a field-goal attempt by
Hayden Epstein, and the game went to overtime. On the first play in overtime, Brady threw a 25-yard touchdown pass to Shawn Thompson, and Epstein kicked the extra point. Alabama quarterback Andrew Zow then completed a 21-yard touchdown pass to Antonio Carter, but Ryan Pfluger's kick for the extra point went wide to the right, and Michigan won by the margin of the missed extra point. In his final collegiate appearance,
Tom Brady passed for a college-career-high 369 yards and four touchdowns. Terrell tallied 150 receiving yards and three touchdowns and was selected as the Orange Bowl MVP. ==Postseason and awards==