Ten-man Dundee became the latest Clydesdale Bank Premier League scalp to be claimed in the Scottish Communities League Cup after crashing out 2-1 to Queen's Park at Hampden.
Sean Burns grabbed the winner for the Irn-Bru Third Division side after a Jamie Longworth penalty had cancelled out Steven Milne's early opener, as Neil McGregor saw red for the visitors.
Kilmarnock, Hibernian and Ross County were all dumped by lower league opposition last night and their fate was shared by Dundee, who were without four of their new signings for the second-round tie.
Martin Boyle was cup-tied following his move from Montrose, while Lewis Toshney and Mark Stewart both missed the clash through injury and Colin Nish was not named in the squad.
Queen's were without long-serving striker Tony Quinn, who failed to recover from injury in time after a late fitness test.
Dundee were threatening after a couple of minutes when Milne's cut-back found John Baird and his close-range effort cannoned off the body of James Brough.
At the other end, the home side almost had the net bulging when Longworth raced onto a Michael Keenan ball and looped his effort across the gaping goal and just wide of the post.
The visitors were ahead with just five minutes on the clock when Baird teed up the shot for Milne and he rifled past the grasp of goalkeeper Neil Parry into the bottom corner.
Dundee could have doubled their advantage soon after but Ryan Conroy hooked just over the crossbar from six yards.
The Dark Blues were hit with a double blow instead when referee Brian Colvin pointed to the penalty spot for a foul on Longworth, before showing McGregor a straight red card for the challenge.
Longworth recovered to step up for the spot-kick himself and drove low past Rab Douglas from 12 yards with 24 minutes gone.
Queen's could have been ahead when a Burns free-kick from 25 yards found its way past a number of bodies in the box only to bounce off Douglas' legs.
Dundee also had a decent chance to restore their lead just before half-time when a powerful shot from Conroy was just tipped over the crossbar by a full-stretch Parry.
It was Douglas who was called into action after the restart when he did well to prevent Brough's effort from a Burns corner from finding the back of the net.
Dundee could have been celebrating when a long ball from Jim McAllister was met on the volley by Baird but he was off-target with the ferocious effort.
Queen's Park still looked dangerous and an Andy Robertson shot took a massive deflection before falling narrowly past the upright before they surged into the lead.
Longworth was the provider with a perfectly-timed pass for Burns who unleashed from just inside the box, leaving Douglas with no chance after 76 minutes.
Despite some late pressure from Dundee, Queen's held on for an impressive victory.