After the 1899 season, Ferbert resigned as Michigan's head coach to travel to Alaska to participate in the Klondike Gold Rush.

Three Michigan players were named to the 1899 College Football All-America Team, as selected by The Philadelphia Inquirer: end Neil Snow, halfback John McLean, and tackle Richard France.

Fullback Leo J. Keena scored Michigan's first touchdown less than two minutes into the game, and the kick for goal was unsuccessful.

Michigan scored two more touchdowns in the second half, the first on a short run by Ebin Wilson with Neil Snow kicking the goal.

After 15 minutes of play in the first half, right tackle Allen Steckle scored a touchdown on a short run, and Neil Snow kicked the goal.

In the second half, Charles Frank Juttner, a substitute right tackle, scored on a "revolving play" from the one-yard line, and Snow again kicked the goal.

[6] On October 18, 1899, Michigan defeated Notre Dame by a 12–0 score before a crowd of 2,000 spectators at Regents Field in Ann Arbor.

A large crowd that included university president James Burrill Angell attended the game at Regents Field.

After a scoreless first half, right tackle Charles McDonald scored a touchdown on a short run to cap a 50-yard drive.

Two special trains from Ann Arbor delivered the football team, band, and students to Detroit's Michigan Central Station on the morning of the game.

[10] The playing field at Bennett Park was in good condition despite snow and rain that fell the prior day.

Michigan's touchdowns were scored by Richard France, Hugh White (two), Clark Leiblee, Allen Steckle (two), and Charles McDonald.

Although Michigan lost by a final score of 12 to 11 on Penn's Franklin Field, the Wolverines gained national respect with a good showing against the Quakers.

The latter team, although beaten, was not disgraced, for the Western boys made their Eastern rivals work hard for every inch of ground they gained.

"[13]The game also featured a duel between two of the best centers in the country, Penn's Pete Overfield and Michigan's William Cunningham.

Cunningham had much the better of it during the first half, but in the second period Overfield, through better staying qualities, made big holes through Michigan's bulky centre.

"[13] On November 18, 1899, Michigan defeated Case Scientific School by a 28–6 score at Regents Field in Ann Arbor.

Michigan's starters, including John McLean and Charles Street, were put into the game in the second half, and the Wolverines scored 23 unanswered points during that period.

[15] On Thanksgiving Day, November 30, 1899, Michigan lost to Wisconsin by a 17–5 score before 22,000 spectators at West Side Park in Chicago.

Excursion trains brought fans from Wisconsin and Michigan, and the brass bands from both schools also attended.

[16][17] There were reports that Michigan's strategy was to put O'Dea out of the game, and he was subjected to a number of rough hits by Richard France and William Cunningham.

A Wisconsin newspaper account described the incident as follows: "Meantime O'Dea had been laying out France, hitting him with such force that the big guard was stretched out and but for the time gained through the wrangle at the end of the goal line and the speedy ending of the half, would hardly have been able to continue playing.