The Knights won the conference title in 1992 with a 9–1 record overall, earning entry into the NCAA Division III Football Championship.

Carleton played its first game against the University of Minnesota in 1883, making it the tenth-oldest football program in Division III.

[3] Carleton insisted that a member of the faculty be allowed to play and that the game would be rugby style football.

Minnesota's coach Thomas Peebles preferred the soccer style of play, but agreed to the conditions as long as he could act as the referee.

[9] In the 1915 season, Carleton outscored Stout, Cornell, Grinnell, Macalester, Beloit, and Hamline by a combined score of 323–0.

"[6] When Hunt left for the University of Washington in 1917, Carleton hired Cub Buck as his replacement and as athletic director.

[15] By the fall of 1917, the Great War had reduced the number of athletes on campus and Carleton slipped from its previous success.

1918 was a very unique season due to the flu pandemic and Student Army Training Corps program.

A joint Carleton-St. Olaf team played the University of Minnesota; due to a lack of cohesion of the Northfielders, they lost 59–6.

[12]: 192–6  During his three-year tenure at Carleton, Buck played pro football with Jim Thorpe and the Canton Bulldogs on Sundays after coaching on Saturdays.

On the next play, the Oles ran the ball and the swarming Carleton defense caused a fumble in the end zone which they recovered for a touchdown.

The Knights were Midwest tri-champions in Beson's first year, and the team put together four impressive seasons, going 21–7–2, and outscoring opponents by 632–397.

[32] After several more winning seasons, Carleton left the Midwest and rejoined the Minnesota Intercollegiate Athletic Conference in 1983.

The team was 9–1 overall and was selected to play in the Division III playoffs that year, but lost 20–8 at Central College (Iowa) in the first round.

[1] During the 2010 football season, the Cannon River, which flows directly behind Laird Stadium, flooded to record levels.

[44] The Knights' biggest rival is the Oles of St. Olaf College, located on the other side of Northfield, Minnesota.

Due to the Great War and the flu pandemic, the rivals combined forces to play the University of Minnesota at the beginning of the 1918 season.

[12]: 194 The rivalry has continued every year since except during World War II and after the Halloween blizzard in 1991, when St. Olaf refused to reschedule the game.

[49] The trophy name is based on both schools being top national liberal arts colleges, Carleton #6 and Macalester #26 in the 2017 U.S. News & World Report rankings.