Surprising teams own nation’s longest losing streaks after huge upset

On Thursday night, the UMass Minutemen toppled the Rutgers Scarlet Knights 37-21 despite being 29.5 point underdogs.

It was the Minutemen’s first win since Oct. 26, 2024, a remarkable upset for a team that’s long been down on its luck.

Despite the fun story, there are a few top-tier college football programs that probably wish it never happened.

Now, with UMass back in the win column, Oklahoma State has the longest losing streak in the country at 11 games.

It’s been more than a year since the Cowboys last won a game on Aug. 28, 2025, against UT Martin, as detailed by u/Efficient-Freedom517 on Reddit.

And OK State isn’t the only team now looking over its shoulder.

The Arkansas Razorbacks and Purdue Boilermakers both have 10-game losing streaks going into the 2026 season, with both teams last winning on Sept. 6, 2025, against Arkansas State and Ball State, respectively.

Fortunately for those teams, though, they’re well positioned to end those streaks before they hit a full year.

The Boilermakers had a 17-point lead on Indiana State on Friday when this story was published, and Arkansas is set to face off against the North Alabama Lions on Saturday as 40.5-point favorites.

The Cowboys, meanwhile, may face a more difficult test.

They face the Tulsa Golden Hurricane on Saturday, a team that bested them 19-12 last season in Stillwater.

This time, they’ll have to win on the road to break their losing streak.

In their defense, they are favorites, but only by 5.5 points.

That relatively slim margin for a power conference program against a group of six team is not only due to last year’s game; it likely reflects the tumult in Stillwater.

This season, the Cowboys added 91 new players to the roster under new coach Eric Morris.

Will those players have jelled enough in the offseason to right the ship?

If they haven’t, Oklahoma State’s hold on the longest losing streak in college football will continue for at least another week.