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.
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