The 2026 season opened with Game No. 990 on Aug. 27, as Winona State traveled to NCAA Division I St. Thomas and suffered a 15-9 setback.
A few weeks later, the Warriors reached another milestone in Game No. 992, meeting Jamestown for the first time in program history. Winona State controlled the contest, earning a 28-0 victory on Sept. 12.
Game No. 994 provided one of the season's biggest highlights. The Warriors hosted No. 20 Augustana and came away with a thrilling 42-41 overtime victory, securing their first win over a nationally ranked opponent since 2022.
Winona State entered its Nov. 7 home finale with a 3-6 record before delivering a dominant performance in Game No. 999. The Warriors defeated UMary 55-7 to reach four victories on the season and set the stage for the program's historic 1,000th game.