The Wildcats, who last won against Morehead State on Nov. 25, are also off to the first 1-5 start for the program since 1926-27, according to ESPN Stats & Information research.
Back then, the Wildcats played in the Southern Intercollegiate Athletic Association and finished 3-13 under Basil Hayden in the coach's first and only year with the team, which was mostly comprised of football players. Three years later, the team hired Adolph Rupp.
On Saturday, Kentucky led for 24 minutes and 40 seconds, but a stalled offense, foul trouble and turnovers opened the door for North Carolina's late 13-5 rally that turned the game.
From the 12:07 mark to the 4:01 mark in the second half, Kentucky failed to register a field goal. The Wildcats finished 3-for-13 from the 3-point line and shot just under 40% from the field overall. North Carolina's numbers were similar except for turnovers. Kentucky finished with 16 to UNC's 11.
Keion Brooks, who is injured and didn't play Saturday, volunteered to speak with the media after the game, saying his teammates weren't "up to it" following the loss.
"We need to get our swagger and our confidence back," Brooks said. "That's what I'm really worried about."
Added Calipari: "You're talking about guys that are going through stuff that's really, really hard for them -- to take responsibility, to own their performance, to accept where they are on the team."
The subdued coach also cited immaturity as one of the culprits in his team's loss.
Cam'Ron Fletcher, a freshman, was visibly upset and emotional at the end of the game after playing just two minutes.
Calipari said Fletcher later apologized for his "attitude."
"You've got to accept your position on this team," Calipari said. "Cam was mad he didn't play more. I said, 'The guys in front of you are playing.' Cam came in and apologized after."
During the team's previous four losses this season, Calipari preached hope and the value of additional experience in this unconventional season. He spoke of hope on Saturday too, but largely focused on the mistakes made by his team.
He also didn't say he knew exactly how to fix it.
That might suffice in other parts of the country, but Saturday's historic low will only magnify the frustration within Big Blue Nation, which hasn't enjoyed a Final Four run since 2015 and hasn't watched its favorite team win a national title since 2012.
Calipari said his players didn't compete as if they believed they were still in the game down the stretch.
Brooks said the Wildcats "didn't deserve to win."
Next up for Kentucky? A matchup next Saturday against rival Louisville, which suffered an 85-48 loss to Wisconsin on Saturday.
"We've got work to do," Calipari said. "We're gonna have to get this thing right, hopefully shoot the ball better. But this was disappointing. The last 10 minutes were disappointing to me."