For an uncontrollable situation with 2.5 seconds left on the clock, Oklahoma's last chance to forge overtime against No. 4 Missouri went about as well as it could - until Steven Pledger's 3-point shot refused to go down.
Pledger slumped to the ground and put his hands over his face after his potential tying shot clanged off the rim to end the Sooners' 71-68 loss.
Romero Osby was forced to miss a free throw with 2.5 seconds left to set up one last unlikely shot for Oklahoma, and Pledger got the ball when the offensive rebound was tapped back to him on the right wing.
"It was perfect. The play was designed to miss the free throw and get the tip-out and we actually got the tip-out," said Pledger, who led the Sooners with 22 points.
"It was on line. It felt good when it left my hand. It didn't go in."
Marcus Denmon scored 25 points and Ricardo Ratliffe added 15 points and 10 rebounds for Missouri, which claimed first place in the Big 12 with the victory. The Tigers (22-2, 9-2 Big 12) had moved into a tie for first with No. 6 Baylor and No. 7 Kansas by beating the archrival Jayhawks on Saturday night.
"We understand that this game was just as important as the last one," Denmon said. "Pretty much, we have a veteran group and we just wanted to make sure everybody came out and understood how important this game would be for us to play after a big win like the one at home against Kansas."
Oklahoma (13-10, 3-8) still had the ball with a chance to tie with 5 seconds left, after Michael Dixon missed on a drive to the basket. Osby was fouled with 2.5 seconds left and missed both free throws, the second one intentionally.
That completed an uncharacteristic night when Oklahoma missed 14 of 23 free throws, after making 75 percent on the season. Missouri, fifth in the nation at 77 percent, wasn't much better at 10 for 18.
"It's hard to explain because we have shot free throws very well," Sooners coach Lon Kruger said. "When you play the game long enough, it will happen. Unfortunately, it happened kind of with everyone, it seemed."
Sam Grooms had a career-high 17 points and matched his career best with 10 assists, and Andrew Fitzgerald scored 12 for the Sooners.
Michael Dixon chipped in 13 points for Missouri in a game nothing like the teams' previous meeting, won 87-49 by the Tigers on their home court.
Missouri held a 15-rebound advantage in that one but Oklahoma came out ahead 36-22 on the boards on Monday. The Tigers made up for it by holding a 28-12 scoring edge the paint and getting the only 10 fast-break points of the game.
It was Oklahoma's third straight loss at home and fifth in the last six games overall.
"It is frustrating, I know, to the players, coaches and fans - to everyone - to not get the result that we want," Kruger said. "We just have to keep getting better. We keep telling our guys afterwards, 'Good battle and good work,' but we've got to keep doing things from a habit standpoint to have more good possessions in a ball game, enough to get over the hump against good basketball teams."
After rallying to beat Kansas in front of a noisy, sold-out home crowd less than 48 hours earlier, the Tigers arrived to find a half-full Lloyd Noble Center and a student section with dozens of empty seats that had newspapers draped over the backs that the occupants would usually hold up during pregame introductions.
It still got loud when the Sooners pulled within 66-64 after Pledger's 3-pointer from the left side with 3:33 to play.
Denmon followed with a jumper from the right side with 2 seconds left on the shot clock before Grooms and Pledger both went 1 for 2 at the free throw line to get Oklahoma back within two.
Kim English then hit a 3-pointer from the right side off Phil Pressey's seventh assist to provide what proved to be the game-winner with 53.6 seconds left.
Fitzgerald hit two free throws for Oklahoma with 41.6 seconds remaining and Dixon missed on a drive to the basket to give the Sooners their last chance with 5 seconds left.
"We never let them take the lead, and that was a sign of a good team," Missouri coach Frank Haith said. "I think once they made runs, we executed when we needed to make a shot."
The Tigers scored the final six points of the first half and the first six of the second to build a 42-33 lead after Denmon's three free throws.
Dixon's jumper from the right side of the key gave Missouri a momentary 10-point lead before Pledger hit consecutive 3-pointers to get the crowd involved. Oklahoma got within 55-52 after Grooms' jumper from the right wing with 12 minutes left before coming up empty on three possessions with the chance to tie it.
"You want to win at this point in time, right now," Grooms said. "We just have certain plays and certain mishaps on the court that don't allow us to do that right now. ... When we're ready to do it, we'll do it. It's up to us at the end of the day."