Rangers 0-2 Dundee Utd
Dundee United knocked Rangers out of the Scottish Cup with a deserved fifth-round victory at Ibrox.
The visitors took the lead after 16 minutes through Gavin Gunning's powerful header.
Rangers, playing their first match since the departure of top scorer Nikica Jelavic, almost levelled through Sone Aluko and then David Healy.
Johnny Russell fired United's second before the break and Rangers could not find a way back into the match.
The Tangerines will discover their quarter-final opponents on Monday as they seek to repeat their tournament triumph of 2010.
The result ends a disappointing week for Rangers supporters, who saw no replacement brought in for Jelavic, and Ally McCoist's chances of success in his first season as manager are now restricted to the Scottish Premier League.
Jon Daly slid in to try to beat Rangers goalkeeper Allan McGregor to the ball early on and, as it ran loose, Russell tucked away. However, referee Willie Collum brought play back after adjudging Daly's challenge on the keeper as a foul.
United were getting the ball forward quickly in an attempt to stretch Rangers and Russell cut in from the right only to have his shot blocked by a defender.
In another attack, left-back Paul Dixon's swerving shot looked as though it may be going wide but McGregor took no chances and palmed the ball out.
The corner by Gary Mackay-Steven and return cross by John Rankin were both cleared but Mackay-Steven sent in another teasing delivery and Gunning bulleted a header into the net.
The goal awoke Rangers from their lethargy and Aluko skilfully set himself up for a volley that was well saved by Dusan Pernis.
Pernis was called into action again to tip Healy's shot out for a corner.
However, United continued to play with confidence and Dixon played a one-two with Mackay-Steven before releasing Russell into the box and the striker lifted the ball over the advancing McGregor into the net.
Rangers poured players forward as half-time approached and defender Kyle Bartley headed at Pernis after meeting a Steven Davis chip.
Salim Kerkar replaced Mervan Celik at the break as McCoist shuffled his pack and Aluko had a shot deflected wide after working himself some space outside the box.
The home side's attack lacked a focal point and Healy was replaced by Andrew Little before Sasa Papac made way for Gregg Wylde.
In between times, Garry Kenneth could have finished the tie as a contest with a headed chance, the defender looping the ball into McGregor's grasp.
In a rare opening for the hosts, Little scooped a shot over following Aluko's persistence in getting in a cross.
Rankin's dipping volley almost caught McGregor out but the keeper improvised well.
A wayward free-kick by Aluko summed up Rangers' fortunes as United comfortably saw out the win.