It was a couple years earlier, in 2006, his second year on the job. He'd gone just 4-7 in his first year replacing Les Miles, and the pressure was starting to build. The Cowboys were coming off back-to-back losses to Houston and Kansas State when they rolled into Lawrence.
Behind a virtuoso performance by the quarterback-wide receiver combination of Bobby Reid and Adarius Bowman, Oklahoma State rolled to a 42-32 victory. Reid finished with more than 400 yards and five touchdowns passing, and Bowman had 13 catches for 300 yards and four of the scores.
Looking back, it may have been a turning point for Gundy.
"There are games early in a coach's career where a new coach has to establish themselves," Gundy said. "If two or three things go wrong, the doubt could be created, you can't recruit, people who support the program don't believe in you, and then it becomes infectious.
"Those games kind of got us over the hump and we were able to go win a bowl game and enough people bought into the program and keep your head above water."
Everybody knows what has happened since that game.
The Cowboys won seven games the next year, nine each of the next two years, and 11 games in 2010, when they challenged for the Big 12 title. Last year they went 12-1 and beat Stanford in the Fiesta Bowl, coming within a road upset at Iowa State of playing for a national championship.
The Jayhawks mostly have gone the other way since that game in 2006.
They went 12-1 the next year and won the Orange Bowl, but slid each of the next two seasons before Mark Mangino was fired. Turner Gill lasted only two ugly seasons before Weis took over this year, and things haven't exactly gone swimmingly since he drove into town.
The Jayhawks' only victory was over South Dakota State, and they're coming off a 56-16 loss to sixth-ranked Kansas State, their fourth consecutive defeat.
"No one is happy. No one is satisfied with where we are," Kansas quarterback Dayne Crist said. "No one is going to stop and say, 'Hey, well, that's all we've got,' because that's not true. We've always got a little more. We've always got another option and something else we can do. We've just got to keep working."