Lawrence Shankland missed a late penalty as Hearts suffered a Conference League defeat at Cercle Brugge.
The Tynecastle club fell to a 2-0 loss in Belgium on Thursday night.
Scotland international forward Shankland had a chance to equalise with ten minutes remaining on the clock but he sent his spot-kick over the bar.
Malamine Efekele put the home side ahead just before half-time and Gary Magnee doubled their lead in the last minute to make it 2-0.
It was a spirited display from Hearts who will be disappointed that they never took at least a point from the game.
The defeat leaves them 18th of the 36-team table with six points from four games.
Shankland got the first effort on target but his low strike was held and Craig Gordon was the busier goalkeeper in the first half, making several saves.
The forward, who has just one goal to his name this season, had another chance following good wing play from Kenneth Vargas but his back-heel flashed just past the post.
The hosts took the lead in the 40th minute, working a man over on the right side of the penalty box. Efekele mis-hit his first-time shot but the effort wrong-footed Gordon and spun into the corner of the net.
The visitors sprung into action and Cammy Devlin, Shankland, Kenneth Vargas, twice, and Alan Forrest all had shots blocked in the box before the interval.
Cercle captain Thibo Somers headed wide from a good chance but Hearts made a lively start to the second period with Yan Dhanda, Forrest and Vargas all shooting straight at the home keeper.
The lively James Penrice then set up Vargas but the Costa Rica international’s weak effort was saved when he had team-mates in support in the box.
Blair Spittal came on for Hearts as they looked to make their pressure count but one over-hit pass from the substitute spoiled a promising opening and another turnover in possession led to Gordon making an important stop from Paris Brunner.
Hearts got a lifeline when Cercle sub Edgaras Utkus made a complete mess of a headed clearance with his handball eventually leading to a penalty award following a lengthy VAR process.
Shankland went for power and the top corner but the ball flew two yards over right in front of 3,000 visiting fans and Brunner almost put the game out of sight moments later when he crashed the ball off the bar.
The Hearts captain had another chance but flashed a header wide from Penrice’s driven cross.
The game was finally out of reach for the visitors following a last-minute corner. Gordon made a good initial save but was beaten by a major deflection as Magnee’s shot went in off Hearts sub Daniel Oyegoke.
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