Prior to the IHSA Football Championships (1974), Loyola won the Prep Bowl in 1965, 1966, and 1969. Loyola won the IHSA State Championship in football in 1993, 2015 and 2018 and was runners-up in 1992, 2011, 2013, 2016, and 2017. LA football coach John Holecek has led Ramblers to the state playoffs every year since 2006, including three of the last five Illinois State 8A Finals. In November 2011, the Loyola Academy football team lost to Bolingbrook in the class 8A Illinois State championship. In August 2012, the Loyola Academy football team, along with Loyola students, faculty, families and alumni, traveled to Dublin, Ireland to participate in a football tournament. The Ramblers played a Jesuit high school powerhouse from Texas. In a thrilling game with a last minute field goal, the Ramblers fell to the Rangers 30–29. In the Semifinals of the IHSA playoffs, a valiant comeback by the Ramblers fell short. They were upset 27-24 by Glenbard North, finishing the season with a record of 11–2. In 2013, Loyola lost to Naperville Central, 13–10, in the 8A State Football Championship. Loyola beat Marist 41–0 to claim the 2015 IHSA 8A Football Championship on 28 November 2015. On 24 November 2018 Loyola won the 2018 IHSA 8A Football Championship by beating Brother Rice High School 13–3. This was the school third state championship win.