The Cougars finished in 1st place in the MSFA MEL division, receiving an automatic bid to the 1999 postseason NAIA playoffs.
With their success in the regular season, the Cougars participated in their first-ever NAIA postseason playoff.
(8-3 overall, 6-0 conference) 09/11/1999 - With a 42–38 victory over Saint Xavier, the Cougars picked up their first home win in program history today.
10/23/1999 - A 54–36 victory at home against the Trinity International Trojans marked the 4th consecutive win for the Cougars.
The victory completed a perfect 6-0 conference schedule and brought the Cougars their first-ever MSFA MEL title.