Rangers 2 Queen of the South 2 (Queen of the South win 4-3 on penalties): Rangers crashed out of the Ramsdens Cup at the hands of Queen of the South in a dramatic penalty shoot-out after both sides were reduced to 10 men.
The tie was still deadlocked at 2-2 after extra-time but it was Queens who eventually came out on top in an epic night at Ibrox.
The Dumfries side had taken the lead through Nicky Clark, before Barrie McKay levelled for Rangers and substitute Kevin Kyle saw red after just 13 minutes on the park.
Lee McCulloch netted from the penalty spot for Rangers and Queens’ Willie Gibson was also sent off, before Gavin Reilly forced the tie into extra-time with an injury-time equaliser.
The Palmerston outfit came out on top when Northern Ireland striker Dean Shiels and Anestis Argyriou both failed to convert when the tie went to penalties, Ryan McGuffie claiming the decisive goal in the shoot-out.
Rangers made two changes from the side that drew 0-0 with Annan in the Irn-Bru Third Division at the weekend.
David Templeton missed the third round tie after suffering ankle ligament damage on Saturday, while Sebastien Faure was dropped to the bench.
Argyriou returned from injury to claim a starting role for Rangers and Francisco Sandaza was also drafted into the side for the visit of the Second Division leaders.
A minute's silence was observed before kick-off in memory of the 96 who perished at Hillsborough, as fans sent their support to the loved ones of those who lost their lives.
Like Liverpool, the Light Blues also endured tragedy with the loss of 66 supporters in the 1971 Ibrox Disaster.
The second half was just four minutes old when Queen of the South surged into the lead, Clark sending a powerful header past the grasp of Alexander.
Rangers immediately hauled themselves level through teenager McKay after 55 minutes.
Kyle picked up a yellow card just five minutes after coming off the bench and was then shown a red card by referee Stevie O'Reilly with 67 minutes on the clock for a challenge on McGuffie.
Rangers took the lead after 71 minutes when McCulloch converted a penalty after being fouled.
Gibson picked up a second yellow card with a couple of minutes of the regulation 90 remaining for a foul on Kal Naismith.
But Reilly levelled deep into injury time before the minnows went on to rock the home fans.