Dundalk remain without a point in the Europa League after going down to Rapid Wien at the Dublin Arena.
Once again individual errors proved costly for Filippo Giovagnoli's side as their outside hopes of advancing from Group B were killed off by the Austrians.
It was a night to forget for Sean Hoare, who on the 200th start of his career was guilty for errors in the build-up to first half goals for Christoph Knasmüllner and Ercan Kara.
A penalty miss from substitute Nathan Oduwa shortly after the restart was a blow to the home side with Dietmar Kuhbauer's side putting the result beyond doubt just before the hour mark when Kara curled in a superb second.
Chris Shields did pull a goal back for a dogged Dundalk side from a second penalty afterwards but the game was beyond them at that stage.
Giovagnoli, who was forced to watch from the hospitality area of the Aviva due to a touchline ban got his setup wrong on the night with the initial three at the back formation reverting a traditional back four early on before a raft of changes at half-time.
While the Viennese were a class above, ultimately this was a result - like many others - that was given up all too easily.
Dundalk will now turn their attention to Sunday's FAI Cup semi-final away to Athlone Town in the knowledge that this season could yet yield silverware back at the Aviva on December 6th.
There will be two further European matches too, away to Molde in a week's time before the visit of Arsenal to Dublin on December 10th. The hope at this stage will be that their Group B campaign doesn't end up pointless.
The visitors were on top right from the off and could have hit the front after just seven minutes when the impressive Knasmüllner skipped away from Greg Sloggett before teeing Taxiarchis Fountas up for a shot that failed to find the target.
The lead goal would arrive just four minutes later and it was a moment to forget for Hoare. Having got away with gifting possession to Kara seconds earlier, the defender sloppily gave it away again to Srđan Grahovac who released Knasmüllner in space. The former Bayern Munich man then hit a stunning shot to the top left hand corner giving Gary Rogers no chance.
It could have been 2-0 on 18 minutes when another loose pass in midfield allowed Fountas the chance to have another effort on goal but on this occasion the Greek international saw his effort clawed away by Rogers.
Dundalk's first effort on target would arrive a minute later when Mateo Barać's header clear was seized upon by Michael Duffy at the edge of the box. He did well to shift the ball onto his left foot to get a shot away but Paul Gartler was equal to it.
It was largely Rapid who were threatening though with a Kara free kick which had deflected off Sean Gannon in the wall having to be pushed away by Rogers on 28 minutes.
The second goal would arrive eight minutes before the break with Hoare caught out by Schick's cross allowing Kara to head home virtually unmarked.
Dundalk made a triple change at the break with Oduwa, Daniel Kelly and Patrick McEleney all introduced. It almost paid immediate dividends too with a quick free kick by Duffy releasing McEleney on the right three minutes after the restart only for his cross to be headed over by Oduwa.
Dundalk were then thrown a lifeline from the resulting kick-out when Barać was caught in possession and fouled Kelly. Oduwa stepped up to take the spot kick but pulled it to the left and wide with Gartler going the wrong way.
The game then looked over as a contest on 58 minutes when Kara curled a superb effort past Rogers from the edge of the area to make it 3-0 with his second of the game.
After Kelly had snatched at another good chance, the Louth men were then awarded a second penalty on 67 minutes when Grahovac fouled Oduwa. This time captain Shields stepped up and slotted home his spot kick to give Dundalk some hope of a comeback.
Unfortunately for the Lilywhites it was not to be with the best chances after that falling the way of the visitors. Indeed, they almost restored their three goal lead on 76 minutes when Schick saw his shot blocked by Gannon before Rogers clawed away the follow up from substitute Kohya Kitagawa.
Kelly did almost pull another back five minutes from the end when his shot deflected off Ullmann but Gartler was equal to it while Oduwa squandered a further too big chances in stoppage time as Vienna went home with all three points in the bag.
Dundalk: Gary Rogers; Sean Hoare (Daniel Kelly HT), Andy Boyle, Daniel Cleary; Sean Gannon, Chris Shields, Greg Sloggett (Sean Murray 72), Cameron Dummigan (Darragh Leahy 81); Stefan Colovic (Patrick McEleney HT), David McMillan (Nathan Oduwa HT), Michael Duffy.
Rapid Wien: Paul Gartler; Filip Stojković, Maximilian Hofmann, Mateo Barać, Maximilian Ullmann; Christoph Knasmüllner (Yusuf Demir 81), Srđan Grahovac; Thorsten Schick, Taxiarchis Fountas (Lion Schuster 66), Melih Ibrahimoglu (Kelvin Arase 55); Ercan Kara (Kohya Kitagawa 66).
Referee: Tamás Bognár (Hungary).