On Thursday night, the two champs were in position to set up a rematch in the 2023 playoffs, if only they could finish the regular season with victories at PFL 4 in Atlanta.
But it was not to be.
The undefeated Khaybulaev, who needed not just a win but a finish to make the playoffs, got the job done in Round 2 of his bout with Tyler Diamond, securing an arm-triangle choke to clinch his spot.
But in the main event at Overtime Elite Arena, Loughnane suffered a huge upset loss, crumbling to the canvas after Jesus Pinedo landed a jumping knee to the chin 1 minute, 34 seconds into their bout. Loughnane simply needed a win, but instead he was denied a berth in the playoffs.
Instead, that spot went to Pinedo, who after losing his PFL season debut in April needed a first-round finish to secure the fourth and final featherweight seed. He got it, and in stunning fashion.
"The plan was to hunt him down and be aggressive," said Pinedo, a 26-year-old from Peru. "And get the job done as early as possible."
The other featherweight playoff semifinal will pit Khaybulaev against a fellow unbeaten fighter, Gabriel Braga, who scored a first-round TKO of Marlon Moraes, a former champion in the World Series of Fighting and UFC title challenger.
Following what was his seventh straight loss, all by knockout, Moraes announced his retirement.
"I wish I had a better performance," Moraes said through tears, "but I gave all of my heart."
The other weight class featured Thursday was light heavyweight, which lost half of its roster last month because of PED test failures. But the two fighters who were at the top of the standings after early finishes in April's season-opening bouts were not affected by the controversy, and both took care of business again to secure playoff spots.
Josh Silveira grabbed the top seed with a first-round TKO of Delan Monte, who injured his right knee while being taken down by Silveira barely a minute into their fight and could not continue. The quick finish gave Silveira a division-leading 12 points.
Silveira will open the playoffs against Ty Flores, who beat Daniel Spohn by dominant decision, and Hamlet will fight Impa Kasanganay, who made his season debut a success by finishing Tim Caron in the second round with an arm-triangle choke.
Thursday's card was the first of three in June to complete the PFL regular season. Next Friday the heavyweights and women's featherweights take center stage, and June 23 will be an evening of welterweight and lightweight fights.