St Mirren were knocked out of the William Hill Scottish Cup after a 2-1 loss at home to Dundee United.
First half goals from Pavol Safranko and Nicky Clark did the damage despite Saints dominating the second 45.
The Buddies created the first opening of the game with Greg Tansey striking from the edge of the area. However, the midfielder's effort was routine for United goalkeeper Benjamin Siegrist.
United took the lead on 15 minutes as the Saints defence failed to clear their lines follow two great stops from goalkeeper Vaclav Hladky. The Czech stopper blocked Nicky Clark's header and then Safranko's follow-up. But the Buddies could only get it clear as far as the edge of the box where Peter Pawlett had a go. Safranko stuck a toe on it to knock it beyond Hladky and give the visitors an early lead.
The Tangerines were buoyed by their opener and took a firm grip on the game. Calum Butcher headed over from a corner not long after Safranko almost added his and United's second. Then, on 27 minutes, Hladky and Mateo Muzek did well to deny Pawlett and Ian Harkes from making it 2-0.
Ex-Saint Cammy Smith had a go on 31 minutes after driving forward, but his long distance effort for easy for Hladky.
It was a first half to forget for Saints and any hopes of hanging on to just a one goal deficit heading into the interval were extinguished when Clark added a second for the visitors right on the stroke of half-time. A long ball over the top caught out the Buddies defence and allowed Clark to get in between Jack Baird and Mihai Popescu and the striker lifted the ball over Hladky to make it 2-0.
Saints gave themselves it all to do in the second half but started brightly as they looked to find a way back into the match. Oran Kearney had brought on Kyle McAllister and Simeon Jackson in place Greg Tansey and Anders Dreyer.
McAllister looked sharp and had a go two minutes into the second period only for the shot to be blocked. On 56 minutes the winger then floated a ball into the box for Jackson whose header from a tight angle was clawed away by Siegrist.
After a positive start, Saints were given a boost when United were reduced to 10 men just after the hour mark. Calum Butcher was given his marching orders after a poor challenge on Ryan Flynn at the centre circle.
The Buddies almost had a goal back just a minute after the red when Popescu cracked a shot off the underside of the bar that had looked as if it may just had sneaked in.
Brad Lyons and Jackson had curling attempts from inside the box as Saints desperately tried to find a way back into the match - both sent just wide.
Then with 13 minutes to go St Mirren had the goal their second half play deserved. Duckens Nazon scored his first for the Buddies with a strike from the edge of the box deflected off the thigh of Pawlett on its way beyond Siegrist.
Saints had United penned back for the remainder of the match, but try as they may just couldn't fashion the opportunity that would have levelled the scores and taken us to a replay at Tannadice.
Full Time: St Mirren 1-2 Dundee United
St Mirren: Hladky, P.McGinn (c), Popescu, Baird, Muzek, MacPherson (Erhahon 81), Flynn, Tansey (McAllister 46), Lyons, Dreyer (Jackson 46), Nazon
Subs Not Used: Holmes, Corbu, Mullen
Dundee United: Siegrist, Reynolds, Connolly, Butcher, Robson, Seaman, Harkes, Smith (Sow 63), Pawlett, Safranko, Clark (Gomis 65)
Subs Not Used: Laidlaw, Frans, McMullan, Fyvie, Nesbitt
Referee: William Collum
Assistant Referee: David McGeachie
Assistant Referee: Frank Connor
Fourth Official: Steven McLean