A cruel own goal in stoppage time denied Shelbourne a deserved draw at the National Arena in Skopje as North Macedonians Shkendija snatched a 1-0 win at the death.
The League of Ireland champions were worthy of a share of the spoils, the width of a post having earlier deprived substitute John Martin giving them a lead that wouldn't have flattered them.
But with the clock into the second minute of added time, failure to defend a corner came back to haunt Joey O’Brien’s side.
Sebastian Spahiu’s delivery wasn’t cleared, allowing Jamaica international Ronaldo Webster to get on the ball inside the area.
The low cross was then turned into his own net by off-balanced central defender Paddy Barrett.
The frustrating failure to build on their draw with Swedish side Hacken in their opening match meant Shelbourne drop into the elimination places in the 36-team table, ahead of more testing games to come, most notably against Crystal Palace, AZ Alkmaar and Celje.
With Barrett back from a two-match domestic suspension and skipper Mark Coyle back in from the start alongside him in a back three, Shelbourne’s stall looked set up to be one of containment.
But far from it as they echoed the words of head coach O’Brien in demanding they start positively.
That they did, as Kerr McInroy had a shot headed clear by Imran Fetai inside the opening minute.
Shkendija were then stretched by Barrett’s diagonal ball to James Norris on the left and his cross saw Milan Mbeng’s header held by goalkeeper Baboucarr Gaye.
Even though that attack was flagged offside, the early signs were promising for the visitors, who were taking the game to their hosts.
As with Norris on the left, Mbeng was proving a threat down Shelbourne’s right flank, his pace troubling Webster.
It was 29 minutes before Shkendija threatened, Senegalese winger Fabrice Tamba failing to make the most of the time and space he had in blasting high over the crossbar.
A free kick moments later brought a further threat as Shelbourne failed to clear before Alekansder Trumci’s pull back was toed out for a corner by Wessel Speel.
The Shelbourne goalkeeper then had to be brave minutes later when getting out promptly to win a free kick in thwarting Liridon Latifi.
Having grown slowly into the game, Shkendija enjoyed their first spell of possession as half-time approached, though without really troubling Shelbourne, who kept their shape well in what was an evenly contested opening half.
Clearly unhappy with their first-half showing, Shkendija coach Jeton Bekjiri made two changes ahead of the resumption to give his side more impetus.
It worked as they restarted full of energy and invention as Spahiu, one of their substitutes, made space in off the left flank to rifle a shot wide.
Shelbourne responded, pouncing on a misplaced pass in midfield. Harry Wood surged forward, worked a one-two with Mipo Odubeko, only to get under his shot.
O’Brien freshened up his attack on the hour, with San Boyd and Martin on for Odubeko and Wood.
The tenacity of Martin made an immediate impact, as he came inches from giving Shelbourne the lead on 65 minutes.
Having first won the free kick when fouled by Fetai, the striker met McInroy’s arced set-piece only to see his firm header come back off a post and into the arms of Gaye, who was rooted to the spot.
Unfortunately for Shelbourne that was to be the highlight of their night.
An injury to Boyd meant they had to play out the last six minutes or so with 10 men before the sting in the tail of Shkendija’s late winner.
Shkendija: Baboucarr Gaye; Aleksander Trumci, Imran Fetai, Klisman Cake, Ronaldo Webster; Arbin Zejnullai (Reshat Ramadani h-t), Adamu Alhassan (Kamer Qaka 70); Fabrice Tamba (Vane Krstevski 77), Endrit Krasniqi (Fiton Ademi 88), Liridon Latifi (Sebastjan Spahiu h-t); Bejart Ibraimi.
Shelbourne: Wessel Speel; Milan Mbeng, Mark Coyle, Paddy Barrett, Kameron Ledwidge, James Norris (Daniel Kelly 74); JJ Lunney, Kerr McInroy (Ali Coote 82); Harry Wood (John Martin 60), Jack Henry-Francis (Evan Caffrey 82); Mipo Odubeko (Sean Boyd 60).
Referee: Stefan Ebner (Austria).
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