Rangers – relegated to the fourth tier of Scottish football due to financial irregularities – travelled to Tannadice Park full of confidence.

They hold a 20-point lead at the top of the Third Division and fancied their chances of causing an upset against Dundee United, who sit seventh in the Scottish Premier League.

But Johnny Russell had other ideas and gave the hosts the lead inside the first minute.

That was just the start of a disastrous day for Rangers, who were 2-0 down at half-time after Irishman Jon Daly also hit the back of the net.

Russell added a second with 11 minutes remaining before Rangers had both Kal Naismith and Ian Black sent off in the dying stages.

Joining Dundee United in the last eight of the competition were Kilmarnock and St. Mirren, who both won all top-flight ties.

Paul Heffernan's brace fired Kilmarnock to a 2-0 win against Inverness Caledonian Thistle while Portuguese striker Esmael Goncalves also netted twice as St. Mirren beat St. Johnstone 2-0.

Other fifth round results saw Falkirk beat Forfar Athletic 4-1 while Hamilton Academical toppled Dunfermline Athletic 2-0.