LINFIELD failed to become the first Northern Irish team to qualify for the group stage of a European competition after crashing out against FK RFS in cruel fashion.
David Healy's side were denied a piece of history by their Latvian opponents after coming within seconds of securing their place in the Europa Conference League.
Going into the play-off second leg with the scores level on aggregate at 2-2, Linfield put themselves ahead in the 104th minute through Kyle McClean.
And they should have sealed victory at the death in the 120th minute when they sprung a four-man counter attack against a solitary RFS player.
Eetu Vertainen led the charge, as he played in Cameron Palmer ten yards out from goal.
But his weak attempt was easily saved by the goalkeeper, who then started off RFS' counter which led to Jimmy Callacher's dramatic last-gasp own goal.
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Windsor Park fell silent through shock, and that soon turned to despair when RFS beat Linfield 4-2 in the penalty shootout.
Matthew Clarke and Ethan Devine both missed from 12 yards out with Linfield exiting in the cruellest fashion.
Boss Healy wad devastated following the full-time whistle, as the ex-Manchester United striker told BBC Sport: "I don't think I've been as disappointed in any time. Certainly in my managerial career."
Before adding: "It's gut-wrenching. I feel for the staff, I feel for the players, the supporters and everybody involved in the football club.
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"The group stage is where we wanted to be and could – and should – have been there tonight."
Healy was unable to hide his frustration at Palmer's late missed chance which saw RFS go up the other end and equalise.
Healy, 43, remarked: "I'm proud of our performance, I thought we were excellent tonight, some of our play was exceptional.
"It is no crime for a player to miss a penalty, I think the crime that we committed was probably in the 120th minute of the match when we were flooding forward to score a second.
"I have been a player and understand that the opportunity is there, there is nobody tracking, but we have got to either keep the ball, score or kick it into the 20th row of the empty stand.
"We have got to do a bit better, and that is not picking on the players who were breaking – of course there is a hunger [to score]. RFS go up the other end and we concede a poor goal.
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"Again, it is not a crime to concede the goal in the manner that we did because nobody means to and I thought Jimmy when he came on tonight was exceptional.
"He has been an exceptional player for me and for Linfield since he has been here."
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