Sligo Rovers must overturn a one-goal deficit if they are to progress in the Europa Conference League after they were beaten by Icelandic side FH Hafnarfjordur at Kaplakriki.
The Bit O'Red, who created the better of the chances, had Greg Bolger dismissed seven minutes before reigning Icelandic player of the year Steven Lennon netted the Urvalsdeild side’s winner.
Despite defeat and with the away goal rule no longer in play, Sligo will feel they have a chance of advancing from this first round tie, when the teams face each other again at the Showgrounds in a week’s time.
This was Sligo's first European game in six years and the Bit O’Red looked comfortable against their Icelandic opponents in the opening exchanges.
The only change from the weekend’s win over Longford, goalkeeper Luke McNicholas easily claimed Bjorn Sverrisson’s effort early on.
Both sides struggled to manufacture chances and it took until the 35th minute for Rovers to test FH goalkeeper Gunnar Nielsen. The Faroe Islands international was content to see Bolger’s volley from 20 yards fired straight at him following work from Romeo Parkes and Colm Horgan.
There were chances at both ends later in the opening half.
Former Dundalk man Lennon saw his header clip the post from an Ingi Gunnarsson cross on 38 minutes, before both players combined again as the latter fired wide off the outside of his left boot.
Rovers then had their best opportunity of the half in added time, but leading scorer Jordan Gibson was unable to get his shot away after a magnificent scooped pass from Parkes found the former St Patrick’s Athletic winger three yards out from goal.
Gibson flashed a speculative effort across the face of the FH goal on the hour as both camps took their time to settle back into the game after the interval.
Liam Buckley's charges then squandered two golden opportunities to take the lead mid-way through the half.
Parkes inadvertently blocked Gibson’s goal-bound shot after wonderful work from substitute Walter Figueira, moments before Shane Blaney headed straight at Nielsen from a Bolger set-piece.
The visitors were reduced to ten on 77 minutes when Bolger was shown a second yellow card after Maltese referee Ishmael Barbara adjudged the Rovers skipper to have dived inside the FH penalty area.
Rovers were further punished on 85 minutes, with Lennon latching on to the end of substitute Vok Dimitrijevic’s cross as he steered his header into the far corner and beyond the reach of McNicholas.
FH Hafnarfjordur: Nielsen; Kristjansson, Vidarsson, Thorisson, Gunnarsson, Sverrisson, E Jonsson, J Jonsson (Gudlaugsson 93), Helgason (Dimitrijevic 82), Lennon (Hreidarsson 93), Vilhjalmsson.
Sligo Rovers: McNicholas, Banks, Buckley, Blaney, Horgan, Bolger, Morahan, Byrne (Cawley 64), Gibson, Parkes, De Vries (Figueira 64).
Referee: Ishmael Barbara (Malta).