Kentucky football has gone down, up, down, up this century so far. Some seasons have been jam-packed with amazing come-from-behind victories, while some have seen Kentucky go winless in the SEC. No matter how bad Kentucky’s been these past 22 years, one thing has stayed the same: they’ve at least won two games every season. Here we have the best win from each of those campaigns with the final score, spanning several coaches and eras.

The Dark Ages: 2000-2005

• 2000: Indiana (41-34)
• 2001: @ Vanderbilt (56-30)
• 2002: @ #17 Louisville (22-17)
• 2003: @ Indiana (34-17)
• 2004: Indiana (51-32)
• 2005: @ Vanderbilt (48-43)

Ouch. These six seasons featured one win over an AP Top 25 team (out of probably 15 attempts) and just one season with a winning record (2002). The one bright spot for fans during this era was the Indiana rivalry; if you’re going to play a Power 5 school every year, make sure they’re perennially worse than you. The Hoosiers fit the bill perfectly for frequently floundering Wildcat squads.

Bowling Again With Rich Brooks (And Joker’s South Carolina Win): 2006-2010

• 2006: Clemson (28-20)
• 2007: #1 LSU (43-37 3OT)
• 2008: @ Louisville (27-2)
• 2009: @ Georgia (34-27)
• 2010: #10 South Carolina (31-28)

Yes, that is not a typo. Kentucky beat Clemson way back in a different stage of Tigers football in the Music City Bowl. And what UK fan could forget the legendary triple-overtime win over #1 LSU in 2007? Not to mention the crazy comeback over #10 South Carolina in 2010, featuring one of the most exciting finishes in Kentucky history. 2009 was also the most recent year Kentucky defeated Georgia, the only SEC East foe Mark Stoops has yet to beat. Also, I’m pretty sure no other football game has ended with a score of 27-2, or at least not in a long time. But if you ever wondered if there had been one, now you know.

The Rest of the Joker Phillips Era (sigh)

• 2011: Tennessee (10-7)
• 2012: Kent State (47-14)

We UK fans only remember Joker Phillips for two good things: the South Carolina comeback, and the end of the Tennessee streak. Everything else was an absolute dumpster fire. When the “best win” of 2012 was Kent State, you know you are in trouble.

But there was the Tennessee win. After finding themselves up 10-7 late in the 4th quarter while playing a wide receiver at quarterback, Kentucky withstood a late Vol rally and won the game. Fans stormed the field like they’d beaten Alabama. For the first time in 26 years, the ‘Cats had defeated Tennessee and no one had seen it coming. No bowl game? Lousy season? Dismal recruiting class? Mediocre Vols team? Joker still coaching? Didn’t matter. It was time to celebrate.

Small Steps: Beginning of the Mark Stoops Era (2013-2015)

• 2013: Miami (OH)
• 2014: South Carolina
• 2015: South Carolina

2013 was a year to forget, as Joker Phillips left Mark Stoops a team so bad their “biggest” win was a guarantee game against Miami (OH). Do not think the (OH) is for exclamation; it differentiates the Miami Hurricanes from these Miami Redhawks. The years 2014 and 2015 began a nice five-year winning streak against South Carolina, a team Kentucky now has little trouble defeating (at least in football. They are sneaky in hoops). Those wins were nice, but 2016 was when Kentucky really broke through and ushered in perhaps the greatest era of UK football ever.

It’s a Party: The Rest of the Mark Stoops Era (2016-2019)

• 2016: @ #11 Louisville
• 2017: Tennessee
• 2018: @ #25 Florida
• 2019: Virginia Tech
• 2020: @ Tennessee
• 2021: Florida

In any list compiling the greatest UK wins of the last decade, these six games must be included. Beating a rival always feels so, so good, and it’s all the sweeter when no one sees it coming. That was the case in 2016, when the ‘Cats topped the #11 Cards 41-38 after a deep Austin MacGinnis field goal with 12 seconds left. Louisville quarterback Lamar Jackson went on to win the Heisman, but a costly fumble forced by the Kentucky defense gave UK fans the field goal and the most memorable victory they’d known since the LSU days of ‘07. And the best part? It came against Louisville.

2017 saw Kentucky race out to a 3-0 start before the thing happened in Week 4 that we all know happened so I’m not going to write about the thing that happened because we know what happened. Then after two more wins and one more loss the Wildcats faced a Tennessee they knew they could beat. That was the worst part: no excuse for yet another loss in their sad history against the Vols. With under five minutes to play and also trailing by five, Kentucky had to score. Marching into Tennessee territory, the ‘Cats reached the opposing 11-yard line when Stephen Johnson went flying over two Vols to reach the end zone with 33 seconds left. Kroger Field erupted as he hit the pylon. After extending the lead to three with a two point conversion, Kentucky held on to win as Tennessee simply ran out of time. Kentucky went on to lose four of their final five games to finish 7-6, but that was alright. They had hit the jackpot against Tennessee.

Then in 2018 they struck gold again, finally ending The Streak against Florida in perhaps the greatest UK win since the 1970s. The 2018 season had a lot of highlights, but the best moment by far had to be seeing Josh Allen strip the ball from Felipe Franks and Kentucky players storming The Swamp. After that win, fans knew the 2018 season would be special. It certainly was.

And so was the 2019 season, though in different ways. After surviving on the cusp of bowl eligibility for several weeks after star quarterback Terry Wilson went down with a patellar tendon injury in Week 2, the new-and-improved Mark Stoops Kentucky finally began to come around with wide receiver Lynn Bowden Jr. under center. Rebounding from a tough loss to Tennessee to destroy FCS UT-Martin by 43 points, the Wildcats surprised the Commonwealth by piling a 30-burger on 7-4 Louisville to keep the Governor’s Cup. The hype was real going into the December 31st Belk Bowl, where the ACC’s Virginia Tech awaited them with a strong running defense they thought would surely stop Kentucky’s one-dimensional rushing attack.

Well, they were wrong.

Trading points back and forth through most of the first three quarters, it looked like the Hokies would hold on for the win as they took a 30-24 lead midway through the final period. But using one last drive that drained most of the game’s final eight minutes, Kentucky marched deep into Virginia Tech territory before Lynn Bowden chucked it through the air to Josh Ali in the endzone with a mere 14 seconds remaining on the clock. A scoop-and-score on V-tech’s desperation play provided the final margin: UK 37, VT 30. UK fans have probably rewatched the video of Bowden’s pass at least a dozen times. I know I have.

In 2020 the entire season was highlighted by an ultra-rare win in Neyland Stadium over the top-25 Tennessee Volunteers, where the ‘Cats clobbered them 34-7 in one of the biggest beatings the ‘Cats have ever given the Vols. The rest of the season didn’t have much, though they did win a bowl, but this win made up for all the covid difficulties in my mind. Plus Tennessee absolutely cratered after that loss.

2021 was like a repeat of the 2018 joyride in many ways, and while the come-from-behind Citrus Bowl win over Iowa was spectacular, nothing topped the 20-13 home victory in Week 5 over Florida that not only snapped UK’s last streak with the Gators and Vols, but also called for a good ‘ol fashioned field-storming the likes of which hadn’t been seen in over a decade. I mean sure they’d stormed the field before for big wins, but this was a sellout crowd! The entire city ended up on that field!

So there you have it: 22 years of football, 22 different high points. Some years the ‘Cats have reached the stratosphere, like in 2007 and 2018. Others, they took an elevator to the dentist’s second floor, like in 2012 and 2013. One trend to get excited about? The highs of the last four years have lifted Kentucky football into uncharted territories of success that recruits have noticed. Maybe in the next five years Florida will land on this list again, or perhaps Georgia, or (gasp!) Alabama...