Rangers lost more ground in the Scottish Premiership title race as Caolan Boyd-Munce struck late to earn St Mirren a well-deserved 2-1 victory.
Philippe Clement took his side to Paisley aiming for five straight wins to avoid falling further behind in the Scottish Premiership title race.
After losing Leon Balogun to injury early on, their evening took another turn as Butland clattered into Greg Kiltie with the Buddies immediately awarded a penalty with VAR backing up the decision. Oisin Smyth stepped up and made no mistake from the spot.
St Mirren were awarded a penalty after Jack Butland fouled Greg Kiltie
Danilo and Nico Raskin were brought on after the break as the intensity increased and they combined for the equaliser as the Brazilian defender slammed the ball in after Raskin’s effort was blocked.
There was another twist as Boyd-Munce fired into the bottom corner from Evan Mooney’s ball to spark wild celebrations as St Mirren beat Rangers for the first time in 13 years.
The result leaves Rangers 12 points behind leaders Celtic while St Mirren move up to fifth.
More misery for Rangers
Butland conceded a first-half penalty
The early stages were all hustle and bustle before Balogun pulled up with an injury.
The first real goalmouth action of note, however, came when Butland raced out needlessly and unconvincingly to barge Kiltie to the ground as the Saints player went to take control of a long ball.
Referee David Dickinson immediately pointed to the spot and Smyth, who scored a late free-kick winner against Ross County on Saturday, sent the ‘keeper the wrong way with an accomplished penalty.
Oisin Smyth celebrates after putting St Mirren ahead against Rangers
Clement and Vaclav Cerny were booked by Dickinson soon afterwards for complaining too long about St Mirren’s Marcus Fraser blocking off Hamza Igamane’s run to no punishment.
Saints goalkeeper Ellery Balcombe did not have a save to make until he gathered a tame shot by the Moroccan striker just before the break.
Clement had to take action and he brought on Raskin and Danilo for Barron and Bajrami and there was instant improvement.
Skipper James Tavernier came close with a free-kick from 25 yards and then Balcombe saved a shot from Danilo before Cerny crashed a right-footed drive against an upright.
But after making a goal-line save from Danilo, Balcombe was eventually beaten from close range by the Gers substitute as the St Mirren goal continued under siege.
Danilo celebrates after scoring to make it 1-1
Igamane blasted a shot over after combining with Cerny, who then powered in a drive from distance which just cleared the bar.
At the other end Saints substitute Alex Iacovitti and Robin Propper jumped at a corner and the ball rebounded off the near post.
The game swung from end to end.
St Mirren’s Caolan Boyd-Munce celebrates the winner against Rangers
A mistake by Propper allowed Olusanya to race clear, but Raskin got back to see off the danger.
Among the usual plethora of substitutes, 17-year-olds Callum Penman and Evan Mooney replaced John and Olusanya, but it was another replacement, Boyd-Munce, who proved the match-winner in the third of six added minutes.
He met a Mooney pass and drilled a shot low past Butland from 20 yards to sink the Gers.
Clement: Rangers ‘threw away the three points’
Rangers manager Philippe Clement
Rangers manager Philippe Clement speaking to Sky Sports News:
“We threw away the three points today ourselves.
“In the first half we didn’t show enough quality on the ball but also losing a lot of duels and giving away a goal we should not give away.
“You created a lot of belief for the opponent so that’s why I was so angry at half-time.
“I didn’t see that performance coming after the consistency we’ve shown in the last two months.
“We made changes and in the second half the team reacted in the right way and we need to show that every time.”
‘No fear’ for St Mirren
St Mirren manager Stephen Robinson
St Mirren boss Stephen Robinson on Sky Sports News:
“I thought we were terrific in the first half, pressed Rangers really aggressively, had numerous chances and rightly went 1-0 up.
“We started the second half not the way we wanted to. Rangers came onto us, as you would expect a good team to do, and created chances.
“We had to change it and credit to the subs who came on, they changed the game and the never-say-die attitude has to be admired.
“We proved that we don’t need to fear anybody. If you go and play with that intensity you can go and cause lots of teams problems.”