Lawrence Shankland looked devastated after missing a late penalty as Hearts slipped to a 2-0 defeat in the UEFA Conference League to Belgian side Cercle Brugge.
The Scotland striker (pictured by Nigel Duncan) fired the ball over the bar with his right foot with the score at 1-0 in favour of the home side and the Glasgow-born striker looked lost as he gripped his shirt in his teeth in penalty box.
It was a painful moment in a disappointing match for the Edinburgh side who must lift themselves to face high-flying Aberdeen in the William Hill Premiership on Sunday.
Around 3,000 Jambos made the trip for the game and coach Neil Critchley made three changes from the starting line-up against Celtic, Blair Spittal, Beni Baningime and Dainel Oyegoke missing out and Kenneth Vargas, Yan Dhanda and Kye Rowles stepping in.
Cercle Brugge are struggling domestically, they are third bottom of the table, but they are the youngest side in the Belgian league, with an average age of just over 22, and they started brightly with Thibo Sommers seeing his shot deflected for a corner.
The home side pressed high and Frankie Kent showed coolness by clearing the danger on two occasions, but Alan Forrest picked up the ball in midfield and drove towards the Brugge goal. He fed Vargas who laid the ball off to Shankland who tested the home goalkeeper with a low shot.
Brugge were in the ascendancy, controlling territory but not possession, leaving Shankland a lonely figure up top, and Devlin was hurt in a tussle with Aussie countryman, Kye Rowles, in midfield. He received treatment.
Paris Brunner tested Gordon but Hearts broke down the right and Vargas squared the ball to Shankland. The skipper backheeled the ball goalwards. It skidded inches wide of the upright, but this was a real chance for the Capital club.
A succession of free kicks spoiled the game in a sparkly-populated, 29,000-capacity, stadium with little atmosphere, but the Hearts fans behind one of the goals did their best to urge their men on in a low-key game.
Forrest tested Brugge goalkeeper Maxime Delanghe but the ball went quickly to the other end and Brugge opened the scoring after 39 minutes after Hearts failed to clear, Malamine Efekele finding himself free at the edge of the box and he scuffed the ball but it ended up sneaking between Gordon and his left-hand upright.
A bad time to give up a goal, but Penrice galloped down the left and crossed into the box. Devlin fired towards goal and the ball was blocked, Hearts claiming a penalty for handball, but the protests were unheeded by the referee.
Vargas then fired towards goal and again a Brugge defender got in the way. Shankland appealed for a penalty after Vargas was brought down in the box, but it was waved away after a VAR check.
A corner troubled Brugge and the goalkeeper punched clear in a good spell for the visitors who ended the first half on the attack.
The Scots enjoyed 59 per cent of possession in the first 45 minutes and had 209 passes against 150, but they were behind and craved a break, however they were still in the game and Dhanda fired a shot towards goal from outside the box after a move involving several Hearts players.
Felipe Augusto then allowed space on the left edge of the Tynecastle box and Rowles was on hand to clear for a corner, but it was cleared, but Hearts were again struggling to put any pressure on the home side in a contest punctuated by turnovers from both sides in a scrappy game.
Dhanda was robbed just inside the opposition half and Brugge broke but, fortunately, a poor pass in the final third let them off the hook, but seconds later skipper Sommers had a clear sight of goal with a free header and he sent it wide without making Gordon work.
Penrice latched on to a loose ball on the left and Forrest fired towards goal but it was straight at Delanghe and it was palmed away by the goalkeeper at full stretch.
Coach Critchley had seen enough and sent on Spittal and Oyegoke for Dhanda and Forrester.
Brugge also made changes with Christian Ravych out and Edgaras Utkis on with Efekele off and Minda in and it was Vargas who had the best chance of the game so far after great play down the left between Spital and Penrice, but the Costa Rica-born striker again failed to finish.
Hearts were, however, playing the game in the home side’s half but were unable to find the final pass despite pressure from lively Penrice, but it was Brugge who were next to threaten when Brunner burst free and forced Gordon to save with his left boot.
Kent was booked after 70 minutes after a challenge in midfield and the home side made another two substitutions looking for a second goal, Augusto and De Wilde departing and Agyekum and Van der Bruggen going off.
The changes continued with Barrie McKay and James Wilson being introduced after 74 minutes with Boateng and Vargas joining colleagues in the dugout.
However, it was lively Brunner who threatened, dropping his right shoulder and leaving Rowles in his wake before firing wide as the home side turned up the heat. Wilson was fouled of the left near the by line and McKay sent a free-kick into the box, but it was cleared.
Forrest then won a corner on the right and the Jambos appealed for a penalty but the ball was cleared. The referee was sent to the monitor after a lengthy VAR check and a penalty was awarded ten minutes from time, the Jambos first penalty of the season.
Shankland took responsibility and he sent the ball over the bar. At the other end, 18-year-old German striker Brunner, on loan from Ligue 1 club, Monaco, broke and ratted the bar with a shot which had beaten Gordon.
Play raged on and Hearts had a chance when Penrice crossed into the box and Shankland glanced his header wide, another great chance gone. Liam Boyce was sent on for Forrest with less than four minutes remaining, but Hearts failed to break through.
It was Brugge who scored late on to confirm the win as Gary Magnee fired towards goal. The ball hit Oyegoke and deflected wide of Gordon who, seconds earlier, had made a great stop to deny the home side.
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