Beginning in the mid-1990s, the program's senior team, then coached by Jim Mackay, began contending for the Don Sutherin Gray Cup against Hillfield Strathallan College. Appleby and Hillfield would play on each school's homecoming weekend, with the overall winner being decided by total points for and against. The rivalry ended in 2002 when Hillfield discontinued their program. During the same period, the program's junior team experienced great success, which peaked in 2000 when Appleby finished in second place with a five wins and one loss record. The team made and hosted the championship game; however, the juniors lost to Ridley College 7 to 6.