Heart of Midlothian's hopes of playing in Europe after Christmas for the first time since 1989 were dented by defeat against Cercle Brugge in the Conference League.

Malamine Efekele's goal - a scuffed effort that wrong-footed Craig Gordon - just before half-time put the Belgian side ahead.

Lawrence Shankland had a glorious opportunity to equalise from the penalty spot but the out-of-form striker blasted over the bar in the 82nd minute. He has now missed four of his last seven spot-kicks.

Gary Magnee's deflected strike eight minutes later consigned Hearts to a fourth defeat in a row in a miserable season, with only one victory in their last seven games leaving them second bottom of the Scottish Premiership.

Two victories in the Conference League had provided some positivity and gave them a good chance of post-Christmas continental competition, but Cercle's victory leapfrogs them above the Edinburgh club in the 36-team table.

Neil Critchley's side now travel to Copenhagen on 12 December and host Moldovan club Petrocub the following week seeking to secure their place in the top 24 and prolong their campaign.

Shankland and Hearts' misery is going hand in hand this season - and is a stark contrast to the success player and team enjoyed in the last campaign.

The striker's free-scoring form - 33 goals for club and country last season - booked him a ticket to Euro 2024 with Scotland and helped the Tynecastle side cruise to third place in the Premiership.

But he has just one goal in 20 games this season and with no-one else to pick up the slack, Hearts are above bottom club Hibernian only on goal difference.

The fans who made the trip to Belgium will have been forgiven for thinking they had seen this show before, as Shankland drew a blank and the rest of the team looked toothless despite enjoying 60% possession.

Efekele's goal, at the end of a first half notable only for the amount of times the referee's whistle was heard, summed up this season for the striker.

The midfielder - on loan from Monaco, which like Cercle is owned by Russian billionaire Dmitry Rybolovlev – somehow dragged the ball inside Gordon's left-hand post with a weak, scuffed shot.

In contrast, a brilliant instinctive backheel from Shankland went agonisingly past a post with goalkeeper Maxime Delanghe looking beaten.

Shankland blew the perfect opportunity to end his drought and give Hearts a precious point when the home side were penalised for a handball, but his wild effort flew a foot over the crossbar.

The 29-year-old had another chance to equalise moments later from a delightful cross from James Penrice but his glancing header went wide.

Magnee's strike emptied salt in Shankland's wound soon after and means the feel-good factor of Hearts' opening two Conference League wins and the mini bounce new boss Critchley enjoyed are a distant memory.

The Belgian club's fans, players and manager might be wishing they could play Scottish opposition every week.

They are enduring equally as poor a season as Hearts, sitting 14th out of the 16 teams in the Belgian top flight.

And prior to the win against Critchley's side they had gone three games without a victory - and were thumped 5-0 by Anderlecht in their previous home game.

However the victory against Hearts puts them close to securing European football into 2025, and follows a draw and a 1-0 win against Kilmarnock in Europa League qualifying earlier this season.

Miron Muslic's side face a trip to Olimpija before a home game against Istanbul Basaksehir and - having enjoyed a six-game unbeaten run at home prior to the Anderlecht game - they will fancy their chances of picking up the point that might well keep them in Europe.

Hearts head coach Neil Critchley: "It was a hugely disappointing result.

"Nothing in the first half, not many chances at either end really, fine margins.

"We conceded a poor goal in the first half and then I thought in the second half we were better, some good moments we didn't take and things not quite going for us."