Fenwick Football is a Chicagoland football powerhouse that has produced many great players and teams in its history. Among those are 1953 Heisman Trophy Winner Johnny Lattner.

Prior to the institution of a state playoff system for football in the 1970s, Fenwick competed to play in the Prep Bowl, which pitted the champions of the Chicago Catholic League against the champion of the Chicago Public League. Fenwick won four Prep Bowl titles at the game's usual home of Soldier Field. The first was in 1945 where a crowd of 80,000 fans saw Fenwick defeat Tilden High School, 20–6. This game is currently tied as the 7th most attended high school football game. The second win was in 1962 when Fenwick defeated Schurz High School 40–0. The win not only capped an undefeated season but was played before over 91,000 fans—the third largest crowd to witness a high school football game in Illinois history.

In the modern era of Illinois High School Football with the inception of the IHSA State Championship (1974), Fenwick has had three(3) teams reach the State Semi-Finals (1981 6A, 1995 5A, and 2016 7A) and two teams reach the State Quarter Finals (2004 5A, and 2014 7A).

Fenwick Football, who now calls Triton College their football home, continue to represent the Friars with PRIDE!

Recent History
2012 -2013-2016-2017 League Champions 
2012- 2013 7A  Second Round Playoffs
2014 7A State Quarter Finalist
2016 7A State Semi-Finalist
2017 7A Playoff Qualifier
2019 5A Playoff Qualifier
2021 5A State Champions