Kentucky football's 4 biggest "what ifs" since 1999

Kentucky football has had its share of heartbreaks and near misses as well. While the Wildcats have seen historic highs, like the 2018 Citrus Bowl win, like the basketball team, there are a few moments that leave fans wondering, what if? (If you are interested in the basketball what if, you can read that here)

Here’s a look at some of the most tantalizing what-ifs in Kentucky football since 2000.

1. What if Kentucky beat Tennessee in 2018?

This one hurt a lot. The 2018 Wildcats were one of the most successful teams in program history, finishing 10-3 and ranked No. 12 in the final AP poll. However, a midseason stumble against a struggling Tennessee team leaves the fans questioning what could have been.

• The scenario: Kentucky entered the game 7-2, riding high after a win over Missouri. Tennessee, meanwhile, was 4-5 and would go on to lose its final two games to finish 5-7.
• The result: Kentucky fell flat in Knoxville, losing 24-7 in a game where the offense sputtered, managing only a late third-quarter TD to avoid a shutout.
• The fallout: Without that loss, Kentucky would’ve finished the regular season 10-2, with its only losses to ranked teams Georgia (No. 5) and Texas A&M (No. 19). Could the Wildcats have earned a New Year’s Six bowl bid to the Fiesta or Peach Bowl instead of the Citrus Bowl (which resulted in a win)? The Cats would have almost surely cracked the top 10.

2. What if the Bluegrass Miracle never happened?

Perhaps the most infamous gut-punch in Kentucky football history, the 2002 loss to LSU still stings.

• The scenario: Kentucky led LSU 30-27 with just two seconds left. LSU’s offense, led by Marcus Randall, needed a 75-yard miracle.
• The result: A desperation heave deflected off a Kentucky defender and landed in Devery Henderson’s hands for a touchdown. LSU won 33-30, leaving Kentucky fans in disbelief and Guy Morriss wet after a premature Gatorade bath.
• The fallout: Kentucky finished the season 7-5 but missed out on a bowl game due to NCAA sanctions. Had the Wildcats secured the win, they’d have an 8-4 record with a marquee victory over LSU to use in recruiting.

3. What if Tim Couch stayed one more year?

Tim Couch rewrote the record books during his time in Lexington, but what if the star quarterback had returned for his senior season in 1999 instead of declaring for the NFL Draft?

• The scenario: Under Hal Mumme, Couch led one of the most explosive offenses in college football at that time, throwing for 4,275 yards and 36 touchdowns in 1998.
• The result: Without Couch, Kentucky stumbled to a 6-6 record in 1999, missing out on bowl season. With him under center, it’s easy to imagine Kentucky reaching new heights and potentially contending for a major bowl berth, or at least getting back to a bowl game to keep the momentum going.

4. What if the refs had called the delay of game in 2014 and Kentucky stopped Florida’s streak sooner?

Kentucky’s 31-year losing streak to Florida haunted the program for decades. While the Wildcats finally ended the drought in 2018, what if they had managed to snap the streak earlier?

• The scenario: Several close calls during the streak stick out, but none more than the 2014 game in Gainesville. Kentucky, led by quarterback Patrick Towles and head coach Mark Stoops, pushed Florida to triple overtime.
• The result: A controversial delay-of-game penalty wasn’t called on a critical Florida fourth-down conversion in overtime. The Gators scored on the next play and eventually won 36-30.
• The fallout: If Kentucky had won, it would have been Stoops’ first signature SEC victory and a major program-defining moment in just his second season. The Wildcats finished 5-7 that year and missed a bowl game, but a win in Gainesville could have propelled them to a stronger finish, a bowl game, and accelerated Stoops’ rebuild.

Why These Moments Matter

For Kentucky fans, these what-ifs underscore how close the program has been to even greater success. While they can’t change the past, they fuel hope that future Wildcats will make the leap when similar moments arise.

What are your biggest what ifs in Kentucky football? Share your thoughts with Big Blue Nation below!