Rangers plunged deeper into crisis after crashing out of the William Hill Scottish Cup as goals from Gavin Gunning and Johnny Russell secured a 2-0 win for Dundee United at Ibrox.
Ally McCoist's men had already exited the Champions League, the Europa League and the Scottish Communities League Cup, meaning the Clydesdale Bank Premier League title is now their only hope of silverware this season.
McCoist himself was the last Rangers player to score a winner against United in the Scottish Cup back in 1989 and lack of resources up front following the deadline day departure of Nikica Jelavic was painfully evident as they ended this tie with a front pairing of Salim Kerkar and Andrew Little.
Russell had the ball in the net for United after a couple of minutes but the effort was disallowed when referee Willie Collum ruled goalkeeper Allan McGregor was fouled by Jon Daly in the build-up. At the other end, Sone Aluko had a go from distance after collecting from David Healy but dragged the shot across the face of goal and wide of target.
The visitors still looked dangerous and Russell threatened again with a deflected effort that was claimed by McGregor, before the Rangers number one saved well from Paul Dixon at full-stretch.
But United were celebrating with 15 minutes gone when Gunning met a Gary Mackay-Steven cross and sent a firm header past McGregor from eight yards.
The visitors scored again after 35 minutes when Dixon slipped the ball into the path of the unmarked Russell and he took advantage of the space to rifle high past the grasp of McGregor.
After a less than inspiring performance, Celik's involvement came to an end after just 45 minutes when he was replaced by Kerkar for the second half.
Little - whose injury problems meant his last game for Rangers was in October 2010 - then replaced Healy to partner Kerkar up front as the Ibrox side battled desperately to haul themselves back into the tie.
Little could have sparked a late comeback when he met a Sone Aluko pass only to blast over the crossbar from six yards.