In November 2018, Loyola Academy beat their first three playoff opponents, including two shutouts, and qualified for their ninth IHSA 8A semifinals in the last ten years. Loyola went on to beat Brother Rice 13–3 in the 8A final game on November 24, 2018. Underdogs Loyola beat the 14th, 6th (10-1 Maine South), 3rd (undefeated Oswego), 2nd (12-0 and reigning 8a champion Lincoln Way East) and 1st seeds (13-0 Brother Rice) during their playoff run. Holecek said. “They fulfilled something I will always remember, one of the most special seasons of my life. Nothing is going to beat this in my career."