Heart of Midlothian failed to pose a threat in a 2-0 UEFA Conference League defeat against FC Copenhagen to leave their hopes of progress resting on their final game.
Amin Chiakha opened the scoring just after the break and Craig Gordon kept Hearts in the game before being penalised with a controversial penalty award.
Kevin Diks netted from 12 yards in the 78th minute to seal three points which moved the Danish league leaders above Neil Critchley’s side in the table.
Hearts have now lost three consecutive games in the competition after winning their opening two matches. The result left Critchley’s side close to the elimination line but they round off their league campaign at home to struggling Moldovan side Petrocub next Thursday.
Copenhagen had knocked out Kilmarnock in the qualifiers and they imposed themselves on the game early on.
There were two scares for Hearts around the 10-minute mark, both of them coming from Brazilians. Gabriel Pereira was allowed a free header but could not keep it down and Gordon denied Robert with his foot.
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Robert and Mohamed Elyounoussi were both causing problems and the former Celtic winger almost got on the end of a return pass in front of goal only for James Penrice to get in front and knock the ball to safety, although only off the crossbar.
Hearts escaped a decent penalty claim when Frankie Kent bundled Chiakha over with his arm but the challenge came at a cost as the defender injured himself in the fall and hobbled off in apparent pain.
The half ended without Hearts managing a shot at goal and only managing one touch in the opposition box.
The Danes made their superiority count in the 48th minute. Right-back Diks dribbled his way into the box and set up Elyounoussi, whose shot was brilliantly saved by Gordon. The rebound broke for Chiakha to knock home from close range and the goal was given following a lengthy VAR check for offside. The striker was ahead of the Hearts defence but just behind the ball when Elyounoussi shot.
Copenhagen would have been out of sight in the subsequent five minutes had it not been for the brilliance of Gordon. The 41-year-old stopped Thomas Delaney’s close-range header with his foot before throwing himself at Chiakha’s goal-bound effort from 10 yards.
Hearts really struggled to give their 3,000 travelling fans anything to shout about. Their only shot at goal came from Cammy Devlin and was deflected well wide. The closest they came was when Copenhagen defender Pantelis Hatzidiakos glanced a header on to roof of his own net from James Penrice’s corner.
Any hope the visitors had of sneaking a result was extinguished when Italian referee Fabio Maresca pointed to the spot after being shown very limited footage of a collision between Chiakha and Gordon.
The 18-year-old got his toe to the ball before Gordon got his hands to the ball and the forward ran into the Hearts goalkeeper. The referee had initially blown for a free-kick to Hearts and completely reversed his decision after a brief watch.
Diks sent Gordon the wrong way from the spot and the game drifted to a conclusion.