Kentucky's five biggest games in the last 25 years

Note that these are not Kentucky's biggest "wins" of the last 25 years. The most important consideration? The stakes and the anticipation heading into the game based on what each meant for the program historically.

5) No. 22 Penn State vs Kentucky, 1999 Outback Bowl

The Tim Couch era was a very different time for Kentucky football. The 'Cats were on the cutting edge of the sport's offensive revolution, had a Heisman-caliber quarterback and a style of play that made the Wildcats a headache to game plan for.

The defense was lacking and UK was only 7-4 and unranked. Given those facts and with this as a bowl game, the end point rather than an open horizon ahead, this game cannot rank as high as some of the others.

But given how much the program's fans had suffered over the years this rates high. Remember also, at this point in time many believed Kentucky was on the move in the SEC with that new brand and fan engagement was very high. There was a sense that much better days would lie ahead.

One could mention the Citrus Bowl against Penn State roughly 20 years later but this first matchup followed a longer period of relative dormancy and because of Couch and the Air Raid at that moment in the sport's history the game was very significant.

4) No. 1 LSU vs No. 17 Kentucky, 2007

While these Wildcats had dropped a game at South Carolina they were back in the top-20 and armed with the kind of offense that ensured the Tigers would not overlook their trip to Lexington.

LSU had won a national championship just a few years prior and this team was loaded with future NFL players.

ESPN was in Lexington and CBS covered the game because it felt like Rich Brooks' long march toward relevance was paying off and leading to something big. Turns out it did. In terms of capturing national attention and putting UK in a position to make lots of national noise this game has to be very high on any list, even if hindsight plays a part in it.

One could make a case for this game being even higher.

3) No. 6 Georgia at No. 11 Kentucky, 2018

The first really big matchup between Mark Stoops and Kirby Smart came late in the 2018 regular season. That game between Kentucky and Georgia was the de facto SEC East Championship Game, with the winner almost assuredly bound for Atlanta.

Though we know UK would go on to lose to a hapless Tennessee team on the road the next week, the 'Cats still would have been in Atlanta if they had beaten Georgia.

Kentucky fans will have to hope this year's game goes better than that one. Kentucky's best team in roughly 40 years wasn't much of a match for a Georgia team that really came to play with a strong performance.

2) No. 7 Kentucky vs No. 15 Florida, 2007

No hindsight here. Put yourself back in the mindset at that time and this game makes a lot of sense, even ahead of UK-LSU the previous week.

Kentucky had just upset the No. 1 team in the nation, was 6-1 (2-1 SEC), and had climbed to No. 7 in the polls even after an earlier loss to South Carolina.

LSU went on to win the national championship as a team with two losses. Had Kentucky defeated Florida it could have served as an energizing rallying cry to help propel the 'Cats to a different finish to the season. Maybe not, but at this point in the season UK still had a chance to play itself into national championship conversation.

We only know from hindsight that the defense and depth were not good enough to do that.

1) No. 11 Kentucky at No. 1 Georgia, 2021

This isn't recency bias. The only reason someone wouldn't put this here is if they don't actually believe in their team, right?

6-0 vs 6-0? No. 1 vs. No. 11? SEC East probably on the line. Playoff talk faintly detectable as background noise? Georgia is excellent and the line is jarring but this one has to be the top choice because every possibility is open. Kentucky is coming off back to back wins against Florida and LSU.

If Kentucky were to win this game there would be a case for UK to be No. 1 in the country.

We limited the scope of this list to the last quarter-century but given Kentucky's history from 1977 (its last SEC championship) through the late 90s this could really almost go back all the way to the Bear Bryant era.