Monaghan recorded their first SFC victory over Tyrone since 1988 after a drama-filled afternoon at Clones .
The defending Ulster champions, who had lost all five previous championship encounters against Mickey Harte’s team in the last decade, hung on to win 1-12 to 0-14.
Tyrone goalkeeper Niall Morgan missed a free in the last minute of normal time which could have forced a replay, and instead it is Monaghan who go forward to play Armagh in an Ulster semi-final on June 28.
Tyrone were furious at referee Eddie Kinsella’s decision to play only two minutes of injury-time after an action-packed second half which saw three black cards shown in the last 11 minutes.
Darren McCurry (Tyrone) and Monaghan pair Dermot Malone and Darren Hughes all received black cards late on.
Monaghan led by 0-8 to 0-7 at half time having also missed a penalty and an open goal in the opening period.
The sides were level six times during that time, with Monaghan taking the lead for the first time through Conor McManus’ free after 26 minutes.
Kieran Hughes missed an easy goal chance in the fourth minute when Tyrone goalkeeper Niall Morgan soloed out of goal and then hand-passed the ball straight to him, but the full-forward kicked it wide with the net gaping.
Hughes was again involved in a crucial moment when referee Eddie Kinsella awarded a penalty against Tyrone defender Ronan McNabb for a foul on Dessie Mone.
Hughes’ penalty crashed off the upright, with Morgan beaten, and Tyrone cleared the danger.
Mattie Donnelly was impressive for the Red Hands and scored three points from play while Kieran Hughes also kicked a brace of points for last year’s Ulster champions.
Dermot Malone grabbed the decisive score of the game with the only goal after 41 minutes.
Dick Clerkin’s crossfield kick found Darren Hughes, who cut inside and fed Malone who came inside and hit a low finish to the corner of the net.
Fintan Kelly’s second point of the game stretched Monaghan’s lead to 1-10 to 0-8 after 47 minutes, but Tyrone fought back with scores from Mattie Donnelly and McCurry.
Monaghan were hanging on at the death but deservedly booked their place in the Ulster semi-finals.
“It was a big thing hanging over the players’ heads that they hadn’t beaten Tyrone for so long,” said Monaghan boss Malachy O’Rourke.
“We scrambled across the line in the end up but that was as good as doing it any other way.
“All it does is get us through to the semi-final and Armagh will be sitting there waiting for us.
“We have to get our heads down, that is the cruel thing about football, no-one will pat you on the back for the last day, we will get our heads down straight away and look forward to the next day.”
Meanwhile, Tyrone’s assistant manager, Tony Donnelly, insisted there had not been enough added time had been played.
“There were quite a lot of stoppages at in the last 15 minutes, last 10 minutes in particular,” he said.
“Of course if you are the team coming from behind you want more additional time but it is doubly frustrating when there is a stoppage in additional time.”