Twenty-five years later, Pitino is heading back after another unbelievable run -- one capped with an amazing late-game rally that left his old protege wondering what the heck happened.
Freshman forward Chane Behanan made the go-ahead basket with 1:06 left Saturday and Pitino's fourth-seeded Louisville Cardinals outscored Florida by 15 points over the final 10 minutes for a 72-68 victory in the West Regional final.
And all Pitino could think afterward was, "Hate to do that to ya, kid."
"Tonight, it was very difficult because of the way the game ended, because they outplayed us for 32 minutes," Pitino said. "And it really hurt inside. As much as I felt like celebrating, it really hurt because he did such a masterful job of coaching."
Russ Smith, who finished with 19 points, followed Behanan's bucket with a pair of free throws and then Florida freshman Bradley Beal and teammate Kenny Boynton each missed chances to tie in the final seconds.
Louisville made one more free throw to seal the game and reach its ninth Final Four, the second under Pitino, despite playing the final 3:58 without point guard Peyton Siva, who fouled out.
Seventh-seeded Florida (26-11) went out in the regional final for the second straight year, with Donovan falling to 0-7 lifetime against the man who coached him on that Final Four team at Providence in 1987, hired him as an assistant at Kentucky a few years later and felt as proud as a papa when he watched Donovan win his two national titles in 2006 and 2007.
"I said this earlier, for myself, I don't think any of us like losing," Donovan said. "But if someone said to me, `You have to lose a game, who would it be to?' I would say him."
Louisville will take an eight-game winning streak on its trip New Orleans. Awaiting is a possible matchup with Pitino's old school, Kentucky, which will have to get by Baylor on Sunday to set up a grudge match to end them all.
"We think they're excellent. We think they're great. I coached there. It's great. Great tradition," Pitino said. "But we want to be Louisville. We have a different mission. They have a different mission. But we both want to get to a Final Four and win a championship."
This game had a much more warm-and-fuzzy story line than that possible Bluegrass State matchup -- a meeting between two men who say theirs is more of a father-son relationship than anything else.
But make no mistake. This was no heartwarmer.
Donovan got under Pitino's skin early in the second half during a timeout when he worked over the officials, who promptly called a foul against the Cardinals (30-9) when play resumed.
"He called that," Pitino shouted to the ref. "Why don't you just give him a whistle?"
Pitino couldn't get a break for a while after that and when Siva picked up his fourth foul, the coach stomped onto the court and got hit with a technical. Erving Walker made four straight free throws and the Gators led by 11, setting the stage for what could've been Donovan's fourth trip to the Final Four.
But the team that went 8 for 11 from 3-point range in the first half went cold -- really cold -- not hitting any of nine attempts from beyond the arc in the second.
The Gators missed six shots and committed one turnover over the last 2:30. They didn't score after Boynton's layup gave them a 68-66 lead with 2:39 left. They finished with 14 turnovers to six for Louisville -- probably the difference in a game in which they still outshot Louisville 50 percent to 45.
"What happens is, you can't lose confidence," Pitino said. "I kept telling our guys we're going to the Final Four. Win the Big East tournament, we're going to the Final Four. And they did."
They did it with a team pretty much void of stars.
But the game's best freshman on this day wasn't Beal, but rather Behanan, who was far less heralded than the Florida star coming out of high school, but outplayed him down the stretch when the trip to New Orleans was on the line.
The freshman from Cincinnati scored 13 of his 17 points in the second half, including nine over the last 8:02 and Louisville's last two field goals -- both after Siva had fouled out with nine points and eight assists.
Beal, meanwhile, matched Erik Murphy with a team-high 14 points and controlled this game for the first 37 minutes.
But over the last 3, he tried twice to take the ball to the hoop, only to get denied by 6-foot-10 center Gorgui Dieng. Beal missed the desperation 3 in the waning seconds and also got called for traveling after stealing a wild pass from Smith while Louisville was nursing a one-point lead with 18 seconds left.
The Gators came into the tournament losing four of five but won their first two games in the NCAAs by an average of 30. They looked as though they'd be playing in the Superdome next weekend, but then they fell apart.
"It was a tough journey for us. I think we stuck with it and we played together as a team," Beal said. "We got this far. I'm real proud of our guys. It's just unfortunate we ended up losing today."
In the first half, Donovan looked like the better coach, though anyone would look good when his team is shooting that way. The Gators went 8 for 11 from 3, 6 for 10 from inside the arc and constantly harassed Louisville en route to a 41-33 lead.
But Pitino didn't become the first coach to take three programs to the Final Four for nothing. He scrapped the zone defense, had his players get up in the face of the Gators and it worked -- though the Cardinals paid the price in foul trouble.
Behanan and Kyle Kuric each finished the game with four fouls. When Siva got his fourth and Pitino got his `T,' the coach tried to settle things down, stepping up to Siva and saying, "It was a foul. Stop saying it wasn't."
Whether he believed it or not, who knows?
As for whether he thought a comeback was possible, especially playing the final 4 minutes without Siva on the floor? Well, Pitino did say in the lead-up to this game that the 1987 trip to the Final Four made him believe anything's possible.
This is his first trip back since 2005, when Louisville also played a clunker of a first half against West Virginia -- but rallied for an improbable win.
This one had a different feel at the end, because this one was between family.
The coaches shared a quick hug at center court after the final buzzer.
"I said, `Billy, I feel bad. I feel terrible, man,"' Pitino said. "He said, `Are you kidding me, Coach? I am so happy for you.' That just doesn't happen in this world."