At Tennessee, Alabama and Ole Miss, Lane Kiffin has found ways to break UK fans’ hearts

The list of high-level SEC football coaches that have found success against Kentucky in their careers is not short.

But it would be difficult to find one who has been quite as adept at dealing losses to UK in particularly heart-breaking fashion as Ole Miss head man Lane Kiffin.

Kiffin has won all three of his career meetings with the Wildcats as coach of Tennessee and Ole Miss by one possession. Two of those wins came in overtime.

“I don’t know if I’d make too much of that because every year is different, and our teams have changed a lot,” Kiffin said Sunday when asked about recent close games against Kentucky. “It doesn’t mean it won’t come down to the last play this time, but I think both our teams are different than they were a couple of years ago.”

Still, while the sample size is not large, history has shown Kiffin’s teams making the plays in key moments that Kentucky could not.

To make matters worse, while offensive coordinator at Alabama, Kiffin led the charge in flipping quarterback Mac Jones from UK to the Crimson Tide. Jones went on to lead Alabama to a national championship before being drafted in the first round of the NFL draft by the New England Patriots.

Here is a closer look at Kiffin’s history versus Kentucky.

Tennessee 30, Kentucky 24 (Nov. 27, 2009)

In Kiffin’s only season as Tennessee head coach, he brought a 6-5 Volunteers team to Lexington for a senior night game viewed as UK’s best chance in some time to end what was then a 24-game losing streak in the series.

Earlier that season, Kentucky had earned its first win at Georgia in 32 years. Tennessee had been blown out 42-17 at Ole Miss just two weeks earlier.

Kentucky led 21-14 at halftime behind a stellar showing from Tennessee native Randall Cobb, but it gained just 80 yards of offense in the second half. When a Tennessee fumble gave Kentucky possession with 2:21 remaining at the Volunteers’ 37-yard line, the Wildcats were unable to find the end zone for a possible game-winning touchdown, instead settling for a 23-yard field goal to send the game to overtime.

Rich Brooks’ Wildcats got the ball first in overtime but were quickly stymied before Lones Seiber missed a 49-yard field goal attempt short. Three plays later, Tennessee running back Montario Hardesty scored the game-winning touchdown on a 20-yard run.

Ole Miss 42, Kentucky 41 (Oct. 3, 2020)

Playing in front of just 12,000 fans due to COVID-19 restrictions in the second game of the 2020 season, Kentucky led 28-14 five minutes into the second half before giving up three straight Ole Miss touchdowns.

Kentucky rallied to tie the game at 35 with a Chris Rodriguez 1-yard run with 2:04 left in regulation and opened overtime with a 10-yard touchdown run from quarterback Terry Wilson, but kicker Matt Ruffolo missed the extra point attempt. When Ole Miss matched UK’s touchdown on its first overtime possession, it needed just a Luke Logan extra point to secure the victory.

“Ever since I got here he says Coach Kiffin owes (Ruffolo) a present for missing a (kick),” linebacker Jacquez Jones later joked after transferring from Ole Miss to Kentucky . “I can’t do nothing but thank Ruffolo for that game.”

Ole Miss 22, Kentucky 19 (Oct. 6, 2022)

Kentucky actually entered the last matchup against Kiffin as the higher-ranked team at No. 7 in the Associated Press Top 25, but Kiffin and the No. 14 Rebels still prevailed thanks in part to two Will Levis fumbles in the fourth quarter.

The second of those fumbles came one play after what appeared to be a game-winning touchdown pass from Levis to Dane Key with 58 seconds remaining was nullified by an illegal motion penalty. Special teams were an issue again as Ruffolo had an extra point blocked and another point-after attempt ruined by a bad snap. Ruffolo also missed a field goal earlier in the game, and UK took a safety after punt returner Tayvion Robinson allowed a kick to bounce to the UK 1-yard line.

After UK offensive coordinator Rich Scangarello boasted earlier in the week his offense was built to handle pressure, Ole Miss was credited with nine tackles for loss and three sacks. On one of those hits, Levis suffered turf toe that would derail his final season at UK.

“They were motivated all week by their offensive coordinator saying bring the blitz, and we’ll light you up,” Kiffin said in the postgame interview with ESPN. “There you go.”

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