Hibernian missed out on UEFA Conference League qualification as a stoppage-time own goal by Miguel Chaiwa handed Belgian side Gent a 3-2 victory at Easter Road.
David Gray's team were on course to reach the league phase of European competition for the first time in their history after goals from Jason Kerr and Felix Passlack had turned the match around following Josue Vergara's first-half opener.
However, Christian Burgess equalised for Gent with six minutes of normal time remaining before Chaiwa turned an El Hadji Seck cross into his own net in time added on.
The defeat saw Hibernian join fellow Scottish Premiership clubs Rangers and Motherwell in failing to negotiate the Conference League play-offs.
Gent create early chances at Easter Road
Gent arrived in Edinburgh as seasoned operators in European competition, having reached the league phase of the UEFA Conference League in four of the previous five campaigns. Hibernian, who play in the Scottish Premiership and host matches at Easter Road in Leith, were seeking to reach the league phase for the first time.
The visitors looked the more assured side in the opening exchanges, moving the ball patiently through the thirds of the pitch to create the first opening of the match. Abdelkahar Kadri took aim from the right edge of the Hibs penalty area, but his shot was well blocked by Adam Mayor.
Hibernian were forced to adapt without attacker Owen Elding, who was ruled out of the squad after failing a late fitness test before kick-off. Martin Boyle provided an initial response for the hosts when he turned smartly inside a crowded penalty area, seeing his shot deflected just over the crossbar.
Gent quickly reasserted control and should have taken the lead in the 12th minute. Swedish wide man Momodou Sonko broke free down the left flank after Passlack failed to track his run and flashed a low cross across the face of the six-yard box. Unmarked forward Vergara looked certain to score but mistimed his lunge and failed to connect with the ball.
Sonko remained a threat shortly after, having a shot bravely blocked by Chaiwa before Tibe de Vlieger fired wide from the edge of the box after being given space by the Hibs defence.
Vergara strikes after Lowe misses opener
Hibernian squandered a prime opportunity to open the scoring in the 27th minute. Boyle played a perfectly weighted reverse pass to send Nathan Lowe racing clear behind the Gent defence. The on-loan Stoke City striker had only goalkeeper Davy Roef to beat but scooped his shot over the bar from 14 yards out.
Gent capitalised on the reprieve as the home side grew ragged in possession. Matties Volckaert had a shot held by Hibs goalkeeper Raphael Sallinger, before another dangerous cross from Sonko picked out Vergara, who headed straight at Sallinger.
The Belgian club took the lead six minutes before the interval. Left-back Tiago Araujo surged forward down the flank to deliver a cross into the box. Vergara turned brilliantly and struck a rising left-foot shot that Sallinger touched but could not stop from flying into the roof of the net.
Boyle attempted to rally the home crowd before half-time, cutting in from the left wing and forcing Roef into a good save at his near post to keep the score at 1-0 at the break.
Disallowed goal and Hibernian comeback
Hibernian thought they had equalised two minutes into the second half when Boyle bundled the ball home from close range after Josh Mulligan's mis-hit shot bounced into his path. However, Spanish referee Juan Munuera reviewed the incident on VAR and disallowed the goal for handball, prompting angry protests from Gray, who was shown a yellow card.
The crowd of almost 19,000 at Easter Road found its voice again in the 56th minute when Hibs drew level. A corner was cleared as far as Jamie McGrath on the edge of the area. Volckaert blocked the Irish midfielder's initial shot, but McGrath gathered the rebound and floated a cross from the left to the back post, where Kerr rose to head past Roef.
Hibs pushed forward with greater urgency, with head coach Gray urging a cup final level of intensity. Midfielder Mulligan drove forward and forced a save from Roef. Gent almost restored their lead at the other end when Burgess headed against Sallinger's left-hand post from a Mathias Delorge corner kick.
Late drama and stoppage time heartbreak
The hosts completed the turnaround in the 77th minute. Passlack played a sharp one-two with Mulligan before driving an angled shot past Roef into the net to give Hibernian a 2-1 lead.
Gent refused to yield and brought themselves level with six minutes of normal time remaining. Substitute Laszlo Benes delivered a corner into the penalty area, and Burgess rose to head the Belgian side level at 2-2.
Disaster struck for Hibs in stoppage time. After coughing up possession cheaply, the home side were caught on a rapid Gent counter-attack. Seck delivered a low cross across the face of goal, and Chaiwa, under pressure from Ibrahima Cisse, turned the ball into his own net.
Chaiwa's night ended in further misery moments before the final whistle when he was shown a second bookable offence and sent off, sealing Hibernian's exit from European competition.
