In their eighth season under head coach Amos Alonzo Stagg, the Maroons compiled a 16–0–2 overall record, which included four practice games against high school football teams.
Chicago defeated Wisconsin by a 17–0 score to claim the undisputed championship of the Western Conference.
[1] On September 23, 1899, Chicago opened its intercollegiate football season with a 40–0 victory over the team from Knox College.
[5] On October 7, 1899, Chicago played to a 5–5 tie against Iowa that finished the season undefeated with an 8–0–1 record.
Chicago, playing without its captain Kennedy, was unable to score a touchdown and tallied its five points on a field goal by Henry.
One Chicago newspaper account called the game "a triumph of the West over the East; a demonstration of the effectiveness of the style of football played in this section of the country.
Chicago touchdowns were scored by Slaker (1), Hamill (3), Henry (2), Wellington (1), Sheldon (1), and Ahlswede (1).
[11] On October 28, 1899, Chicago played Penn to a 5–5 tie before a crowd of 8,000 persons at Marshall Field.
The Penn team that traveled to Chicago was one of the Big Four teams from the East with a lineup that included four first-team All-Americans: quarterback John H. Outland [namesake of the Outland Trophy], center Pete Overfield, halfback Josiah McCracken, and guard Truxtun Hare.
[12][13] The game was reportedly marred only by "incessant coaching" from the Penn sideline; the conduct was met with "hissing" from the crowd.
The Times of Philadelphia proclaimed: "Never has Marshall Field been the scene of a more bitter struggle; never have two athletic forces contended with more heroic courage in the Western metropolis, and never a greater foot-ball battle witnessed in the West than today's Pennsylvania-Chicago game.
"[14] The Sunday Inter Ocean reported: "Never before has such an exciting game of football been played in Chicago.
The Chicago Sunday Tribune described right halfback Ralph Hamill as the star of the game, reporting that he scored four touchdowns (the Sunday Inter Ocean reported he scored five) and "raced up and down the field for touchdowns and long gains continually", including a run of 65 yards.
Chicago's touchdowns (four points each) were scored by Slaker, Cassells, Feil, Place and Hamill.
The game began shortly after 2:30 p.m. and was played in halves of 35 and 30 minutes, the second half having been shortened due to darkness.
The Daily Inter Ocean described the game as the "leading social function of the day" with the field a "bedlam of noise" and female Chicago students "out in force with large bows of maroon ribbon dangling from their umbrellas and barrytone tin horns.
"[21] University of Chicago President William Rainey Harper was seated in a central box in the front row and "showed an intense interest in the game.
Guard Frederick Feil was called the "particular star" for Chicago, as he broke out of the pile for long gains on multiple occasions.
The Wisconsin team featured Eddie Cochems at left end, Pat O'Dea at fullback, and Arthur Hale Curtis at right tackle.
The game was played in halves of 35 minutes at Randall Field before 8,000 Wisconsin students and locals with 1,000 Chicago supporters in the east bleachers.