On Saturday, they meet on opposite sides of the court - Pitino trying to make his sixth trip to the Final Four and second at Louisville and Donovan going for a fourth Final Four with Florida.
Pitino is 6-0 in the head-to-head matchups. None, however, has come with the stakes this high or the emotions so mixed. So much of the relationship between coach and pupil has been documented over the years - every time there's an anniversary and, especially, as Donovan's stature rose with his two national titles. After the first one, Donovan celebrated by waving Pitino down onto the court.
Donovan is in his 16th year with the Gators and is back on an upward swing after a few down years following the titles. His most talented player this season? That would be freshman Bradley Beal, who scored 21 points Thursday in the win over the Marquette Golden Eagles that moved the Gators to this point.
"He didn't guarantee me anything when I came in," said Beal, a national high school player of the year. "That's really what drew me into this school and this program is that he really didn't guarantee me anything, and I had to work for it all."
For the Cardinals, this has been a season of ups and downs. They rose as high as No. 4 in the Associated Press poll in December but impressed nobody during a 10-8 Big East regular season.
Pitino has a versatile team with no real superstar. Center Gorgui Dieng averages nine points, nine rebounds, and more than four blocks a game. He blocked seven in Louisville's 57-44 win over Michigan State on Thursday. Point guard Peyton Siva averages 5.5 assists a game and is Pitino's coach on the floor.
Siva says he'd wear a cowboy hat if Pitino asked. "If he told me to put a tutu on in front of ESPN, I'd go do that," he said.
In the buildup to Thursday's Gators-Golden Eagles seminfinal, Marquette forward and Big East player of the year Jae Crowder questioned Florida's ability on the defensive end, and that proved to be a mistake.
The Gators allowed an average of 47.5 points in their first two tournament wins against Virginia and Norfolk State, and the team continued its defensive dominance against a high-scoring, fast-paced Marquette squad.
The Gators held the Golden Eagles to 30 points on 31.4 percent shooting in the first half, and just one point more than their season low of 57.