Let’s be candid. The hardest thing about this column is trying to narrow Kentucky’s heartbreaking losses to merely 6. Most Kentucky fans can recount 6 annoying losses to Florida or Tennessee or under a specific head coach.

In order to make my task more focused, I restricted this task to the years 2000 to present. So no 1965 Houston game when Kentucky lost a bowl bid in hand after QB Rick Norton got his knee shredded, no 1980 game against Tulane when UK lost due to back-to-back (garbage) pass interference penalties that extended the game, no 1987 Tennessee game with Mark Higgs getting stuffed on the goal line again and again, no 1993 Florida game (7 interceptions, yes, 7, but Kentucky still lost) … see what I mean?

But in the 2000s alone, here are 6 losses that still stick in the craw of Big Blue Nation.

6. at Louisville 2000

Any loss to Louisville is about as welcome as a kidney stone for the typical Kentucky fan. This one was worse than most. New QB Jared Lorenzen led UK to a 20-7 first-half edge and looked to have the game in control. A lightning delay stopped the game for an hour and a half, and Kentucky fell apart from there. The game was still in hand late, with an 18-yard field goal set to win the game for UK in the final seconds. Until it was blocked.

In overtime, Lorenzen threw a pick, UofL broke a touchdown run, and Louisville claimed control of the rivalry, winning not only this game, but 5 of the next 6 games in the series. Kentucky went 2-9 and fired coach Hal Mumme after the season amidst NCAA turmoil.

5. vs. Western Kentucky 2012

This game may have been the best indicator of the decline of Kentucky football after Rich Brooks’ retirement. After a nice run from 2006 to 2009 under Brooks, Kentucky fell back to the SEC floor in a hurry. Consider this series with a Western Kentucky team that was transitioning to FBS football when the teams first met in 2008. That game? UK won 41-3. They met again in 2010, and that one was 63-28 UK. In 2011, it was 14-3 UK. But in 2012, on a trick play in overtime, Western Kentucky knocked off UK 32-31. And in four years, Kentucky had seen the margin in the series go from +38 to +35 to +11 to -1, and now was the 3rd-best FBS team (of 3) in the state. Not surprisingly, this was Joker Phillips’ final season as UK head coach, and Mark Stoops was soon on his way to Lexington.

4. at Tennessee 2018

Unlike the other games on this list, this wasn’t a late heartbreaker (although there are plenty of UT losses that would meet that criteria — see 2001, 2006, 2007, 2009, etc.). This was Kentucky’s best team since 1977 coming to Knoxville ranked No. 12 in the nation and as a 5-point road favorite … and completely laying an egg. The 24-7 loss was as sluggish as any performance in UK football history, and when UT missed out on a bowl by following the win with a 33-point loss to Missouri and a 25-point loss to Vanderbilt, it didn’t make most UK fans feel much better. The 10-3 season was nice. But 11-2 really, really should have been the reality.

3. vs. Arkansas 2003

Kentucky won 7 games in 2002 but was ineligible for a bowl due to NCAA violations. In 2003, Kentucky was struggling to try to reach a bowl. The Cats were 4-4 entering a home game with Arkansas. UK trailed 21-7 before UK QB Jared Lorenzen was caught on a live mic telling an early-departing fan, “You’re gonna miss a hell of a game.” Lorenzen wasn’t wrong. He led UK back to a 24-24 tie. And then the game went and went and went: 7 overtimes worth of football, with UK frequently one stop or one 2-point conversion from winning. And at 12:01 a.m., when the game finally ended, it was Arkansas celebrating a 71-63 victory.  UK ended up 4-8.

2. vs. Florida 2017

At that point in time, Florida had won 30 games in a row over Kentucky. The Wildcats, playing at home, had a 27-14 lead with 11:33 to play. Even after Kentucky gave up the lead on a Florida touchdown to a completely uncovered receiver, UK had a chance to win.

A Benny Snell run put UK in position to win on a late field goal — but a holding penalty wiped out the play and left UK just far enough out that Austin MacGinnis’ 57-yard field goal try fell a couple of yards shy of ending that horrific losing streak. This game was hard enough to swallow that it might be No. 1 on this list — except that Kentucky did finally beat the Gators the following year.

1. vs. LSU 2002

For some, it’s the Bluegrass Miracle. For Kentucky fans, it’s a bad dream they can’t wake up from. UK rallied from a 21-7 deficit to take a 30-27 lead on a Taylor Begley field goal with 15 seconds to play.

They had a win over No. 16 LSU in the bag. Until they didn’t.

After a kickoff and an incomplete pass, Marcus Randall heaved the Hail Mary of all Hail Marys, only for the ball to bounce off a couple of UK defenders and fall in the hands of LSU WR Devery Henderson, who took it to the house on the final play of the game. How weird was this game? UK fans were in the end zone, waiting to celebrate.

Instead, they got an up-close look as LSU gut-punched Guy Morris’ UK squad.