Dundalk are 90 minutes away from the Europa League group stages after coming through a nervewracking penalty shootout on a 5-4 scoreline against Sheriff Tiraspol in Moldova.
Chris Shields scored the decisive spot kick as Filippo Giovagnoli's side advanced to the play-offs. They will now face Faroese side KÍ Klaksvik next Thursday.
Things got off to a bad start for Dundalk when they found themselves behind to a Veaceslav Posmac goal after just eight minutes. However, the Lilywhites were the better side after that and deservedly equalised just before half-time through Sean Murray.
There were few notable chances after that but despite tiring in extra-time, the reigning SSE Airtricity League champions held their nerve in the shoot-out with veteran goalkeeper Gary Rogers - who turns 39 tomorrow - making the crucial save to deny Faith Obilor from the spot.
The Louth men made a poor start after falling behind after just eight minutes. After Benedik Mioč's effort was turned around the post by Gary Rogers, Sheriff captain Veaceslav Posmac stole a march on Brian Gartland to send a bullet header to the net from Andriy Bliznichenko’s corner.
The visitors slowly grew into the game and had their first effort on the half hour mark when Michael Duffy cut in from the left only to have his effort blocked by Ousmane N'Diaye.
Four minutes later Murray’s corner picked out Daniel Cleary but he could only direct his header back in the taker’s direction with his shirt being heavily pulled.
The pressure from the SSE Airtricity League champions continued with Chris Shields flashing a shot wide before the equaliser arrived in the first minute of stoppage time.
Michael Duffy found space on the left to cross with Murray stealing in to glance past Zvonimir Mikulić for his first goal since March 2019 to leave it 1-1 at the break.
Duffy and Murray then almost combined for the lead goal on 53 minutes when the former’s cross picked out the run of the midfielder who attempted to back flick it goalwards but unfortunately his effort was blocked by Faith Obilor.
John Mountney, who replaced the injured Sean Gannon after just 13 minutes, then had an effort from range on 65 minutes after Mikulić punched clear Murray’s free kick but the strike was straight at the goalkeeper.
Dundalk briefly thought they had taken the lead on 71 minutes when Duffy’s cross was flicked on by Patrick Hoban for Greg Sloggett to head home at the back post but a free was given against Hoban for an apparent foul on the keeper.
Both sides then had chances to avoid extra-time. Firstly Faith Obilor blazed over in the 89th minute after Gartland’s header clear dropped to him in the box.
Then Daniel Kelly stung the palms of Mikulić before crossing to Duffy whose downward header was cleared on the line by Obilor.
In the last action of normal time Gartland headed wide from Duffy’s corner but a free out was given as extra-time was called for.
Kelly almost turned provider again 30 seconds after the restart when he broke up the right to cross for Sloggett but he couldn’t get enough purchase on the cross under pressure from Posmac as the ball trickled into the arms of a grateful Mikulić.
There was then two scares for Dundalk in quick succession with five minutes to go when Dabney Dos Santos had a shot blocked at close range before Charles Petro pulled a shot inches wide.
In the shoot-out Stefan Colovic and Rifet Kapić opened the scoring for their respective sides but after Hoban had made it 2-1 to Dundalk, Obilor was denied by a brilliant save to his left from Rogers.
Sean Hoare and Patrick McEleney then scored only for Max Veloso and William Parra to reply but, just as he did in the EA Sports Cup final last September, captain Shields stepped up to score the decisive kick and seal the win for his side.
Sheriff Tiraspol: Zvonimir Mikulić; Ousmane N'Diaye, Faith Obilor, Veaceslav Posmac, Cristiano; Andrei Peteleu (Charles Petro 64), Benedik Mioč (Max Veloso 99), William Parra; Andriy Bliznichenko (Rifet Kapić HT), Frank Castañeda, Dimitris Kolovos (Dabney Dos Santos 88). Subs not used: Dumitru Celeadnic, Sebastian Dahlström, Richard Gadze.
Dundalk: Gary Rogers; Sean Hoare, Brian Gartland, Daniel Cleary, Darragh Leahy; Chris Shields, Greg Sloggett; Sean Gannon (John Mountney 13) (Daniel Kelly 88), Sean Murray (Patrick McEleney 72), Michael Duffy (Stefan Colovic 102); Patrick Hoban. Subs not used: Aaron McCarey, Will Patching, David McMillan.
Referee: Aleksandar Stavrev (Macedonia).