St Mirren's dreams of winning silverware this season were ended at the final hurdle as the Buddies fell 2-1 to Dundee United in the IRN-BRU Cup.
Rory Loy cancelled out Tony Andreu's first half opener for Ray McKinnon's side. But Thomas Mikklesen scored with a header to win it for the Tangerines.
United started the opening exchanges brightly with efforts from Andreu and Simon Murray going wide. The latter seeing his attempt go narrowly by O'Brien's near post and come off the side netting.
Stevie Mallan was fouled around 20 yards out after failing to shake off Willo Flood. The award of a free kick in what has become known as 'Mallan territory' was greeted with glee from supporters when the midfielder stepped forward to take.
Loy, on loan from United's city rivals, went closest in the opening 20 minutes when he clipped the outside of the post. The striker nudged himself in front of the defender to get a toe on Lewis Morgan's ball in but could only watch it crack off the woodwork before going wide.
It was Morgan who arguably had the best opportunity of the match when he sent a shot just wide of Cammy Bell's far post. The young winger burst on to a flick on from John Sutton and broke into the box to go one-on-one with the keeper but watched in agony as
United weren't far away from breaking the deadlock moments later when Andreu flashed an attempt just wide of the target. It was a warning sign from the striker who had scored twice at the Paisley 2021 Stadium when the two sides met just over a week ago.
However, it was St Mirren who looked the more likely and a wonderful teasing ball from Kyle Magennis would have yielded the opener had someone in black and white been there to attack. Adam Eckersley picked it up on the left side and swung it back in to meet Magennis who shaped for the shot only for Cammy Bell to smother.
And, frustratingly, United were ahead not long after when that man Andreu did what he had threatened to do when he buried the ball beyond O'Brien. Saints failed to clear their lines and the ball came back to the Frenchman outside the box who lashed the Tangerines ahead.
It could have been a setback but the Buddies weren't going to let it be as they levelled the game straight from kick-off. Sutton took kick off, playing the ball to McGinn who switched the play to Irvine who charged down the right wing before picking out Loy in space. The striker opened up his foot, tucking it into the far corner of the net.
Loy's goal was the perfect response and Saints were back in buoyant mood. Gary MacKenzie had a great chance to put St Mirren ahead just before half time as he climbed above the United defence to get his head on a Mallan corner but sent it wide. It would've been a fitting end to a first half where the Buddies were on top.
Half Time: Dundee United 1-1 St Mirren
The second half looked set to be a cracker after an excellent first 45. But it didn't quite live up to its billing.
Mallan, celebrating his 21st birthday, had a go from a free kick early into the second period after Loy was felled right on the edge of the box. The midfielder elected to go low with the shot but it was blocked by Flood.
There wasn't too much in the way of good opportunities for either side throughout.
With just 15 minutes remaining, United took the lead for the second time in the match. Substitute Mikklesen rose above the St Mirren defence to bullet home Simon Murray's cross. It was a bitter blow for Saints who, try as they may, couldn't fashion any clear cut chances to get back into the match.
Saints went close to grabbing another quick leveller when Mallan curled a shot just wide of the far post.
But it was the Tangerines who looked the more likely to grab a killer third when Ali Coote went close on two occasions only to see one whistle by the post and another well saved by O'Brien.
It wasn't to be for the Buddies and all efforts will now be focused on the vital run-in in the Ladbrokes Championship.
Full Time: Dundee United 2-1 St Mirren
St Mirren: O'Brien, Irvine, MacKenzie, Baird, Eckersley, Magennis (O'Keefe 84), McGinn, Mallan, Morgan, Loy, Sutton
Subs Not Used: Langfield, Stelios, Webster, Fjelde, Whyte, Watters
Dundee Utd: Bell, Durnan, Edjenguele, Murdoch, Flood, Telfer, Robson, Coote (Donaldson 89), van der Velden (Mikklesen 58), Andreu, Murray (Nicholls 80)
Subs Not Used: Zwick, Dixon, Toshney, van der Struijk
Referee: Nick Walsh
Assistant Referee: Sean Carr
Assistant Referee: Gary Hilland
Fourth Official: Steven Kirkland
Attendance: 8,089
