He accepted a football scholarship from Montana Technological University, where he received All-Frontier Conference honors as a quarterback and punter.
His team eventually lost 35–56 in an NAIA Division II playoff game, after the Oregon Institute of Technology accomplished the biggest comeback in school history, by scoring 49 points in the second half.
Against Southern Oregon University, he set school records for passing yards (411) and touchdown throws (6) in a single-game, while leading his team to a 52–50 win.
In 1991, a training camp knee injury to starting quarterback Timm Rosenbach, allowed Kupp to gain additional playing experience.
In his only professional football game, Kupp completed 3-of-7 attempts for 23 yards in the fourth quarter of the Cardinals' 34–0 loss to the Washington Redskins in week 3.
[9] After starter Troy Aikman suffered a knee injury in the twelfth game against the Washington Redskins, Kupp ascended from third-string to backup quarterback behind Steve Beuerlein.