Dundalk conceded two goals in six minutes to slip to defeat against Russian giants Zenit St Petersburg in the Europa League group game in Dublin.
Robbie Benson’s 52nd-minute goal suggested another famous Dundalk European win was on the cards.
But a poor clearance by Dundalk keeper Gabriel Sava gifted an equaliser to Robert Mak on 71 and Brazilian star Giuliano soon hit the winner
Sava saved an injury-time Mauricio penalty but Zenit had done enough.
Dundalk will look ruefully back on a key moment in the 60th minute when Dane Massey headed a Daryl Horgan cross against the Zenit woodwork.
Eleven minutes later, the League of Ireland champions’ keeper Sava totally miskicked a back-pass from Chris Shields which allowed Giuliano to set up Mak for a close-range finish.
Giuliano hit Zenit’s winner after exchanging passes with Belgian star Axel Witsel but Dundalk remain second in Group D after Maccabi Tel-Aviv’s 2-1 win over AZ Alkmaar.
Dundalk ruffle former Uefa Cup winners
After beating Maccabi two weeks ago to become the first Irish club to win a European group game, Dundalk showed no inferiority complex early on against the 2007-8 Uefa Cup winners, a club reputed to have an annual budget just short of £150m.
Ronan Finn was inches away from putting the Lilywhites ahead on seven minutes after outpacing another Belgian international Nicolas Lombaerts.
Zenit were having the bulk of possession but Dundalk always looked a threat on the break with in-form winger Horgan again showing why he is being linked with a Republic of Ireland call-up.
Former Derry City man Patrick McEleney also showed some delightful touches, with one of his crosses almost resulting in a headed goal for Massey after Luis Neto’s poor defensive clearance.
Benson goal quickly cancelled out by Zenit
The sense that it was going to be another glorious European night for Dundalk increased after Oleg Shatov’s failure to set up a simple finish by Mak in the 50th minute was immediately followed by Benson’s harmless looking shot completely deceiving Zenit keeper Yuri Lodygin.
Zenit were showing signs of panic as Massey headed against the crossbar on the hour but the game turned dramatically 11 minutes later as Sava, preferred to Republic of Ireland squad member Gary Rogers in recent game, fluffed his attempted clearance with Mak punishing the mistake.
As Dundalk began to tire in their seventh game in 21 days, Brazilian Giuliano played a superb one-two with Witsel on the edge of the box before lashing to the net.
Sava saved substitute Mauricio’s weak penalty in injury-time after the same Zenit player had been barged over by Brian Gartland.
But Zenit’s job was done with their next game the return with Dundalk in St Petersburg on 3 November.
What they said:
Dundalk manager Stephen Kenny: “Dane Massey’s header off the post was the turning point.
“Then the (first) goal we gave away was a bad goal. We got punished for it. The second goal they worked it very well.
“The players gave it everything. Their seventh game in 21 days which was really tough going.
“We’ve got to go to Russia next but the game against AZ (Alkmaar) at home is going to be huge for us.”
