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Consider yourself lucky, future Kentucky sports bettors. These moments probably broke some of your hearts. At least they didn’t break your bankroll, too.

As we twist that ladle like a dagger and churn the crust off this kettle of heartache, consider where your cash might have been as you sat there screaming in your Cardinals or Wildcats Starter jackets.

With legal sports betting coming to the commonwealth in September, Gaming Today presents some of the best Kentucky sports bets you (hopefully) never made. (Unless you were rooting for that other school in Kentucky).

Nov. 22, 2022: Vanderbilt 24, No. 24 Kentucky 21

Kentucky sports upsetsThe Commodores had lost 26 consecutive Southeastern Conference games, six straight to the Wildcats.

That didn’t matter much when Will Sheppard caught the eventual winning touchdown pass with 36 seconds remaining at Kroger Field in Lexington. Vanderbilt improved to 4-6, the Wildcats fell to 6-4 in what was trumpeted through the state as one of the worst losses of the Mark Stoops era.

The head coach seemed on board with the assessment, saying: “[I’m] disappointed with the way things have gone. I think everybody is. For whatever reason, I’m not getting it done with this team, getting them in a position to be successful.”

Future NFL Draft green room hostage Will Levis (left) went just 11-for-23 for 109 passing yards and was sacked four times by the Cardinals.

Kentucky entered the game as much as a -650 moneyline favorite with a spread of -17 points. Was that the sound of jubilation over the hill in Tennessee?

Nov. 26, 2016: Kentucky 41, No. 11 Louisville 38

Louisville-football-biggest-upsetsThe Cardinals had been ranked third in the nation before a stunning 36-10 loss to Houston eliminated them from College Football Playoff consideration the previous week. This was the final game of the regular season, time for a bounce-back with no pre-game speech needed from head coach Bobby Petrino as Kentucky strode into Papa John’s Cardinal Stadium. Surely, Heisman Trophy front-runner Lamar Jackson would have a day. Sportsbooks thought so.

Louisville went off as a 28.5-point favorite, was unbeaten straight-up, and was 3-1 against the spread in its last four as double-digit home favorites.

The Cardinals entered the game 12-2 straight-up in its last 14 games in November.

Kentucky was just 2-13 straight-up and 3-12 against the spread in its last 15 games in November.

Actually, yeah, maybe the Cardinals could have used a really good pep talk.

Jackson fumbled the ball away on the Kentucky 10-yard line late in the game, and the Wildcats drove to set up Austin MacGinnis’s 47-yard field goal with 12 seconds left to hand the Wildcats the Governors Cup for the first time since 2010.

It was hard to blame Jackson, but then again it was easy. The future Baltimore Raven Jackson produced four touchdowns and 452 yards, and broke the ACC single-season record for TDs previously held by Clemson’s Deshaun Watson. He also threw three interceptions and lost the eventually decisive fumble.

All the green made this day would have gone into the pockets of the fans in blue.

UAB 76, Kentucky 75, 2004 NCAA Tournament, Round 2

Kentucky basketball upsetsThe Wildcats had been ranked as high as No. 2 in the nation earlier in the season and entered the NCAA Tournament at No. 9, winners of ten consecutively, SEC tourney champs and ranked atop the Midwest bracket.

After dispatching Florida A&M, 96-76, in the first round, Kentucky seemed a logical pick to breeze past Alabama-Birmingham and into the Sweet 16 with a Tubby Smith team that was obviously talented but not laden with stars.

Mo Finley begged to differ.

The Blazer guard hit a 17-foot jumper with 12.2 seconds left, lifting his team to a 76-75 upset. Gerald Fitch’s missed 3-pointer with 2.2 seconds left relegated Kentucky to a 27-5 season that couldn’t be considered a success.

It had been a slog for the Wildcats just to stay in the game under withering defensive pressure.

UAB led by 10 points until a Kelenna Azubuike dunk put Kentucky ahead, 75-74 with 29.3 seconds left and in position to avert the nightmare scenario of bowing out early again as national-title favorites.


Again, Mo Finley begged to differ. And he obviously didn’t care that the Wildcats were a ten-point favorite.

Arizona 84, Kentucky 79, OT, 1997 National Championship

Greatest Kentucky sports heartbreaks


The Wildcats defended their 1995-96 national championship right into overtime as the second-seeded team in the East.

Wildcats partisans and a decent amount of folks understanding how basketball works would note that Arizona was awarded 41 free throws and Kentucky just 17.

That’s not supposed to happen to a Rick Pitino-led team. (Lute Olson, though, not a no-name, either).

Yes, that’s a major disparity. But Kentucky’s Nazir Mohammed missed all six of his second-half free throws, including two in overtime with the Wildcats down two.

Kentucky entered as a favorite of -300 on the moneline and -6.5 on the point spread, according to SportsOddsHistory.

LSU 33, Kentucky 30, ‘Bluegrass Miracle’, Nov. 9, 2002

Bluegrass Miracle



Oh, how those giddy Wildcats fans would have been fumbling with their phones for their favorite sportsbook app when LSU called timeout with two seconds left.

The Wildcats led,30-27, at Commonwealth Stadium in Lexington on Nov. 9, 2002.

The Tigers had one play to cover 74 yards.

Gimme some live odds, no matter how bad! 

While the spread wasn’t in play (LSU closed -5), the ones who’d bet Kentucky on the pre-game moneyline would have been content to just soak in the win and toast their prescience … and the funds about to plop into digital wallets that didn’t exist yet.

None of them could have known that they were just props in the Bluegrass Miracle.

LSU quarterback Marcus Randall didn’t have the arm to span the entire field and everyone knew it. So he heaved from his own 18. Kentucky fans filled the field behind him, heading for the goalposts. Jefferson Pilot Sports was seconds away from posting a graphic proclaiming Kentucky the winner. Wildcats quarterback Jared Lorenzen doused coach Guy Morriss with Gatorade before the pass went up.

It came down closest to a cluster of Kentucky defenders near the 30-yard line, but they tipped it up and forward and into the grasp of wideout Devery Henderson around the 15. With one last-gasp tackle to avoid, he scored.

LSU 33, Kentucky 30.

“Dash Right 93 Berlin” had worked for the win.

It was a bad beat 21 years before you could legally have one of those in Kentucky.

“Bluegrass Miracle” was minted as the moniker of this unforgettable moment — as much as Wildcats fans tried — but among the suggestions in a poll at LSU’s athletics website was “Lexington Longshot.”

And it looked like such a sure bet for those couple of seconds.

Duke 104, Kentucky 103, Elite Eight, 1992 NCAA Tournament

Laettner shot against kentuckyWe all knew it would end here, right?

It’s not that this was even an upset.

Duke entered as a 7.5-point favorite, according to SportsOddsHistory.

Duke, chocked with a roster including hero Christian Laettner, Grant Hill, and Bobby Hurley needed a shot at the horn to win what has been beatified as the greatest game in college basketball history.

But come on.

Kentucky bettors would have actually been breathing again after Sean Woods banked in a shot with 2.5 seconds left for a 103-102 Kentucky lead.

Certainly, they must have thought, Pitino would have his team defend the inbounds pass. He didn’t.

Laettner caught Hill’s uncontested chuck near the free-throw line, faked to his right, whirled to his left with a defender on him, and drilled a 15-foot winner.

For the Kentucky faithful there was and still is that gnawing little ache over this one.

But if sports betting had been legal in Kentucky then, and if they’d jumped on that spread … yeah, it would still hurt.

About the Author
Brant James

Brant James

Senior Writer
Brant James is a senior writer at Gaming Today. He has covered the sports betting industry in the United States since before professional sports teams even knew what an official gaming partnership entailed.

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