Rangers saw their hopes of winning the League Challenge Cup crash as Queen of the South claimed a dramatic penalty shoot-out victory at Ibrox.
The home side looked to be coasting after goals from Barrie McKay and a penalty from Lee McCulloch looked to have sent the Third Division side through after Nicky Clark had put the visitors ahead, but a last minute strike from Gavin Reilly saw the Doonhamers sent the game to extra time.
Ally McCoist was forced to start the League Challenge Cup quarter-final tie without the services of deadline day signing David Templeton after the former Hearts winger suffered ankle ligament damage during their goalless draw with Annan Athletic.
However the Rangers boss did hand a start to Spanish striker Francisco Sandaza, while Queen of the South boss Allan Johnston, a former Ibrox player named himself on the bench for the Dumfries side.
The home side nearly took an early lead as a short back pass by Kevin Holt allowed McKay a shot on goal, but the winger’s strike was smothered by former Rangers youngster Lee Robinson, in goal for the Doonhamers.
Queen of the South had a superb chance to take the lead, as Chris Mitchell received the ball on the edge of the area, but his strike was punched clear by Neil Alexander.
The first half continued with both sides showing little, only a Danny Carmichael strike for the visitors and a Dean Shiels effort for Rangers had the fans attention.
Queen of the South started the second half by opening the scoring, as Willie Gibson raced down the left wing and put a cross straight onto the head of Clark, who powered the ball beyond Alexander and into the Rangers net.
Rangers did get back on level terms, after indecisive defending from the visitors at a corner allowed McCulloch to find McKay six yards out and the youngster was able to slot the ball beyond Robinson for the equaliser.
The Ibrox boss was given a massive headache with less than 25 minutes to go in the game as Kevin Kyle received a red card for a forearm smash on Ryan McGuffie as the two challenged for the ball.
But the Ibrox side did manage to get in front five minutes later as Lewis McLeod played a ball towards McCulloch, who went down inside the box under a challenge from Chris Higgins and the Rangers skipper rose to slot the ball into the net.
With less than ten minutes left the visitors could have got an equaliser as Mark Durnan rose to head a free kick from the right towards goal, but unfortunately his effort smacked off the post and away from danger.
As the game entered injury time Queens were also reduced to ten men as Gibson saw a second yellow card, but that didn’t stop the visitors as with the last kick of the game Reilly got onto the end of a Clark cross to send the game to extra time.
Rangers had chances to kill the game off in the first period of extra time, with Kal Naismith, Lee Wallace and Shiels all going close.
In the last minute of extra time the visitors had a golden opportunity to win the game as substitute Daniel Orsi capitalised on a mistake by Wallace, but Alexander managed to save his strike.
As the game went to the dreaded penalty shoot-out misses by Shiels and Anestis Argyriou saw the Ibrox side crash out.