Legia Warsaw 1 Dundalk 1 (Legia win 3-1 on aggregate)
Dundalk's dreams of becoming the first Irish club to qualify for the Champions League group stage ended following a 3-1 aggregate defeat to Legia Warsaw.
A stunning strike from Robbie Benson gave the Lilywhites hope as they looked to overturn a two-goal first-leg deficit in the Polish capital but an injury-time equaliser from Michal Kucharczyk put the result of the play-off beyond doubt.
Benson smashed a dipping volley into the top-right corner from just inside the 18-yard box in the 19th minute after striker David McMillan had headed Sean Gannon's cross from the right back across goal.
The well-worked early goal was just what Stephen Kenny's side needed but, despite the 67th-minute sending-off of Adam Hlousek, they were unable to find a crucial second which would have forced extra-time before Kucharczyk broke to settle matters.
In an impressive opening period for the Irish champions, midfielder Daryl Horgan saw his well-struck 25-yard free-kick fly straight at Legia goalkeeper Arkadiusz Malarz.
Midfielder Benson then quietened the partisan home crowd inside the Polish Army Stadium when he met McMillan's centre in impressive fashion.
The home side responded though and would have been on level terms on the night minutes later had it not been for a fine save from Dundalk keeper Gary Rogers. Czech Republic international Hlousek connected superbly with a left-footed shot from range but, with the ball heading for the top-right corner, Rogers rose to tip it past the post for a corner.
French midfielder Thibault Moulin was the next to threaten an equaliser, although his effort from distance proved to be a more straightforward stop for Rogers.
Dundalk looked to be facing a mammoth task following last week's 2-0 defeat in Dublin but they almost levelled the contest with 63 minutes played. Horgan surged away down the right and his delivery was nodded down by McMillan only for Benson to direct his overhead attempt over the crossbar.
The Lilywhites' quest for a lucrative and historic Champions League spot appeared to have been made slightly easier when Hlousek pulled down Ronan Finn and was shown his second yellow card in the space of 11 minutes to leave the home side a man light for the final 23 minutes.
Despite the numerical advantage, Dundalk appeared to tire and they looked susceptible to counter attacks.
Substitute Guilherme was the first to threaten when his stinging volley was palmed away by Rogers before Legia wrapped things up in the second of four minutes added on.
Midfielder Kucharczyk raced forward and then retained his composure to cut in from the left and emphatically finish into the right side of the net to spark wild celebrations from the home crowd and condemn the visitors to a place in the Europa League.