Brondby IF 1-1 Hibernian (5-3 on penalties)
Hibernian's return to European competition ended in heartache as they went out of the Europa League on penalties to Danish side Brondby.
Trailing 1-0 from the home leg, captain David Gray's deft finish levelled the tie after 62 minutes.
The full-back was forced off injured but Hibs survived into extra-time.
John McGinn missed Hibs' first penalty in the shootout, and despite Paul Hanlon, Grant Holt and Martin Boyle converting theirs, Brondby took it 5-3.
It was a harsh way for Neil Lennon's side to exit - at the first hurdle - after taking the game to their hosts in the second half and defending bravely throughout.
The Edinburgh club had never won a European tie in 61 years after losing the home leg, but they came close to making history after deservedly prevailing in normal time.
The prize of a tie against Bundesliga side Hertha Berlin however goes to Brondby, who kept their nerve in the shoot-out.
Needing to score to keep the tie alive, Hibs barely created a chance in the first half. McGinn had their one sight of goal in the 18th minute, but Martin Albrechtsen swiftly blocked the Scotland midfielder's effort.
But the visitors were not unduly troubled at the other end either as a defence re-enforced with a third centre-back in Liam Fontaine repelled most of Brondby's attacks.
The hosts' best moments came from set-pieces.
Christian Norgaard and Kamil Wilczek - whose strike after just 16 seconds proved the winner at Easter Road - headed over from corners, while Johan Larsson's curling free-kick was just too high.
But it was 36 minutes before Hibs' debutant keeper Ross Laidlaw - taking over from Otso Virtanen after the Finn's first-leg howler - was called into action.
The 24-year-old conceded five goals on his last outing in April 2015 - for Elgin City against Annan Athletic.
But after missing the whole of last season with a lacerated kidney and being released by Raith Rovers, he showed no signs of rustiness as he tipped a powerful drive from Norgaard over.
Hibs began the second half with greater intent and urgency, McGinn's inviting cross from the left flank headed over by Gray, whose last-minute winner in the Scottish Cup final had sent Hibs into Europe.
But the full-back showed great poise to control and flick home Darren McGregor's prodded ball forward with the outside of his right foot, after Brondby failed to clear Dylan McGeouch's corner.
It was reward for a sustained spell of pressure, but served to stir the hosts into life.
Lebogang Phiri and Svenn Crone both sent shots wide of the target, while Teemu Pukki - a player signed by Lennon at Celtic - found himself in space inside the box but his tame effort was blocked.
Gray's energy and commitment was encapsulated in the driving run out of defence that ended his evening, Norgaard sending the full-back sprawling and landing awkwardly on his shoulder.
Hibs survived some late scares - McGregor escaping with a yellow card when he impeded Pukki's run on goal, while the impressive Laidlaw got a hand to Larsson's effort to divert it wide.
But after neither side threatened to win it in extra-time, Hibs' luck finally ran out.
- 13LarssonBooked at 96mins
- 18PhiriSubstituted forCorluat 102'minutes
- 19NorgaardBooked at 74mins
- 9PukkiSubstituted forStucklerat 114'minutes
- 25JakobsenSubstituted forHolstat 64'minutes
- 23da Silva
- 6BartleySubstituted forForsterat 104'minutes
- 2GraySubstituted forBoyleat 77'minutes
- 35CummingsSubstituted forKeatingsat 90+1'minutes
- 24McGregorBooked at 87mins
- Marius Avram