Dundee United suffered a sickening promotion blow as they lost a goal four minutes into stoppage time to draw with Ross County.
The Tangerines had held the lead from the 12th minute and were the better team but referee Steven McLean’s decision to add on six minutes at the end cost them.
It is now a huge ask for the Tangerines to make it out of the Championship and they will have to do so through the play-offs.
They have only four fixtures remaining to try and close a five point-gap that could go to eight should leaders County beat Dunfermline in their game in hand next Tuesday.
United looked to have given themselves a chance but Jamie Lindsay’s late, late strike knocked them for six.
An explosive strike from Pavol Safranko, who hadn’t scored for seven games, had given United the lead on 12 minutes but it wasn’t enough.
The Tangerines had made four changes to the team that kicked off against Queen of the South on Saturday.
Out went Calum Booth, Rachid Bouhenna, Sam Stanton and Charlie Seaman. In came Paul Watson, Mark Connolly, Ian Harkes and Peter Pawlett.
The Tangerines’ formation was unexpected, with Paul McMullan – fresh for agreeing a contract extension – leading the line. Safranko moved out left and Nicky Clark played in behind McMullan.
The United support, which had been squeezed into a small section of one stand, spilled over into another as well as the fans turned out in decent numbers again.
There was good early pressure from the visitors and the ball appeared to land perfectly for Watson inside the box but he had strayed offside.
Connolly did well to get in the way of a thunderous shot from Lewis Spence on six minutes as the Staggies went on the attack. An angled drive by Danny Armstrong then called United goalie Benjamin Siegrist into action on 10 minutes.
Just two minutes later, the Tannadice team took a dramatic lead.
A mistake by County’s Andy Boyle was pounced on by Harkes, who fed the ball to McMullan. He gave it back to Harkes, who then played in Safranko. The Slovakian international still had plenty to do but he showed great composure to slam a left-foot shot past keeper Scott Fox from 15 yards.
A Pawlett cross from the right on 23 minutes tied the home defence in knots but McMullan couldn’t get on the end of it.
A deep cross from Jamie Robson almost landed on the head of Clark as the match passed the half-hour before the young United full-back was almost punished for losing possession inside his own half when he had time to clear.
United then produced a magical move a couple of minutes before half-time that was worthy of a goal.
Safranko’s pass to McMullan from deep inside his own half was superb. The ball was then flicked inside to Pawlett by McMullan and the former Aberdeen man’s strike was brilliantly saved by Fox.
Six minutes into the second period, McMullan was pulled to the ground by Spence and the former Dundee man was shown the yellow card.
United captain Mark Reynolds – fresh from signing a three-year pre-contract deal with the club – did well to block Josh Mullin’s shot on 56 minutes then his central defensive partner Mark Connolly was the next man booked.
The Staggies brought on ex-United striker Brian Graham to try to change their luck up front but it was the visitors who should have scored again on 61 minutes.
It was yet another terrific ball from Safranko that picked out McMullan but he fired over when he should have at least made Fox make a save.
On 67 minutes, United defender Watson bundled the ball into the County net following Pawlett’s corner but the whistle had already gone for a foul on goalie Fox.
The hosts then made a double substitution, bringing on experienced Don Cowie and Michael Gardyne.
United were sitting a little too deep and County sub Graham went close when he clipped the ball wide at the near post.
The Tannadice men made a change on 77 minutes, bringing on Fraser Fyvie for Clark, and they should have put the match to bed just a minute later.
McMullan it was who nearly made it two when he was unlucky to see his 15-yard strike crash off the post.
United goalie Siegrist to almost sell the jerseys on 84 minutes. His mistake gave Graham the chance to cut it back to Mullin, who appeared to have the goal at his mercy but sent his shot wide.
Having escaped that scare they still had six minutes of stoppage time to navigate. However, they couldn’t hang on and, into the 94th minute, Lindsay slammed a low shot into the net after the ball had bobbled about the United box.
Ross County: Fox, Fraser, Kelly, Lindsay, McManus (Graham 57), Boyle, Mullin, Spence (Cowie 68), Stewart, Van der Weg, Armstrong (Gradyne 68). Subs not used: Munro, Semple, Paton, Grivosti.
Dundee United: Siegrist, McMullan (Smith 90), Clark (Fyvie 77), Safranko, Robson, Butcher, Reynolds, Watson, Harkes, Pawlett (Gomis 90), Connolly. Subs not used: Laidlaw, Nesbitt, Graham, Seaman.
Referee: Steven McLean.