Having no won no fewer than 29 games in any of those seasons, reached three Final Fours and won a national championship, Calipari's expected - much like UK fans - to do much the same with his latest squad, though it was his most inexperienced to date.
It's taken a couple months, but he's reached a point of peace with the fact that this team is different.
"In the last seven, eight years, I have coached teams that have absolutely whomped on people," Calipari said after a 75-65 victory over Tennessee. "And this ain't one of 'em."
Without realizing it, Calipari forgot how to coach something other than a juggernaut. It may have taken a little longer than he would have liked, but Coach Cal is beginning to remember.
"Every game we are going to be in is going to be a dogfight, and instead of going crazy about it, how about just accept it, right, and coach that way?" Calipari said.
For the fourth time in five outings, the Wildcats found themselves mired in a close game in crunch time on Tuesday, and that's what caused it all to sink in for Calipari. Against Louisville, Vanderbilt and Texas A&M, breakdowns and lapses in concentration plagued Kentucky, leading to runs for the opponent, two coming in the final minutes and leading to losses.
On Tuesday, Coach Cal accepted the inevitability of such moments, opting instead to try to lead his team through them.
"I can't imagine this team being up 20 on anybody, because you get up 12, 15, someone will try to steal a ball; they will foul; they will leave their feet," Calipari said.
Sure enough, the Cats were poised to put away the Volunteers after a Nerlens Noel and-one gave them an eight-point lead with 14:33 to play. Kyle Wiltjer then came up with a block and rebound to create a fast-break opportunity for Archie Goodwin. He raced down the floor before leaving his feet to pass to Julius Mays in the corner for an open 3. Mays drilled the shot, but it was nullified by a charging call on Goodwin, the exact kind of mistake Calipari has come to view as inevitable.
"We have been working on him to jump, stop; jump stop," Calipari said. "So he goes driving down the lane, left his feet and threw a wide open pass to the corner. ... But we work every day on jump stops, so there are things that, you know, these guys are growing with."
Of course, Tennessee capitalized, eventually taking a 54-53 lead with just over seven minutes to play. Yet again it was, in Calipari's words, "gut time." This time, however, the Cats didn't wilt.
Just as he tried in vain to do against A&M, Noel sparked his team. With UK trailing for the first time since late in the first half, he hit the first of two free throws before dunking home his own miss. On his way down the court, he showed the kind of fire that makes him perhaps the best candidate to step into his team's leadership void.
"I'm definitely being more vocal with my team, making sure we're on our Ps and Qs and making sure we're together," Noel said.
Leadership is a work in progress for Noel, but he's all the way there in terms of posting unique statistical lines. He did it again against a bruising Vol frontcourt with his 12 points, nine rebounds, six blocks, four steals and two assists while helping to force UT forward Jarnell Stokes to foul out in just 15 minutes of playing time.
"He's a tremendous player and when he's at his best, we're at our best," Wiltjer said. "If he just keeps it up, we're going to be a great team."
The lone columns that remained unfilled in Noel's line score on Tuesday were 3-pointers made and attempted. That's where Wiltjer and Mays came in.
After Noel had inspired the Cats and the Rupp crowd, it was UK's two best outside threats that put UK firmly in control. Mays drilled a pair of 3s in less than a minute - accounting for six of his nine points - to give Kentucky a six-point lead with just over four minutes left.
After Jordan McRae, who led all scorers with 23 points, cut the lead to four heading to the final media timeout, Wiltjer then did something he's never done before.
"You know what's great about Kyle, for the first time since he's been here, he told me to run a play for him, which I absolutely did," Calipari said.
Wiltjer responded by beating his man for a driving layup. His confidence buoyed, he called for the ball once more, drilling a long 2-pointer. From that point forward, UK would lead by no fewer than six points.
"The last couple days we've been running some new plays and they were for me for getting shots," said Wiltjer, who scored a game-high 17 points and hit a pair of 3s. "I knew we had put them in so I just looked over and called it and we ran it."
Calipari installed those plays for exactly those kinds of high-leverage situations because he expects the next two months of Southeastern Conference play to bring plenty more close games. He told his team in the postgame locker room that he's come to grips with the new reality that UK isn't going to be a team that racks up blow out wins.
His players agree, but only to a certain extent.
"We can kind of use that as motivation because we want to be a team that can whomp down on people," Wiltjer said. "There's some things holding us back and we break down, but we're still early in the season. We're a young team so if we just keep improving I think we can."
That's exactly what Coach Cal wants to hear.