AEK Athens suffered a heart-breaking exit from the Europa League after they were beaten at home by already-qualified Zenit St Petersburg.
The Greek side began the day in the box seat to progress to the last-32 as they sat three points clear of Anderlecht in Group G.
But defeat, plus the Belgians' 3-0 win over Hajduk Split, eliminated AEK due to their inferior head-to-head record.
The loss was made even harder to stomach after Ismael Blanco missed a penalty to put AEK ahead, before goals from Alexander Bukharov, Alessandro Rosina and Igor Denisov ensured Zenit's perfect record in the group.
AEK had looked the more likely side to score in the opening period with striker Ignacio Scocco proving a menace.
The Argentinian forced the first save of the match after 15 minutes when his 30-yard effort was tipped over by Viacheslav Malafeev.
Scocco blasted another long-range effort over before he won his side's 39th-minute penalty by inducing Aleksandar Lukovic into a mis-timed challenge.
Blanco spurned the chance to fire his side ahead, however, as his side-footed shot sailed over the crossbar.
It proved a costly miss as Zenit went ahead five minutes later.
Bukharov found enough room to let fly from just outside the area with a left-footed shot that beat Sebastian Saja low to his right.
It stayed that way into the break and with Anderlecht 2-0 ahead in their home tie with Hajduk, AEK knew they needed to earn a point to progress.
Scocco continued as their main threat after the break, firing a free-kick into the wall before forcing another save from Malafeev.
The Argentinian was, however, playing a lone hand and Zenit started to exert pressure of their own with Bukharov forcing a sharp save before Saja kept out an close-range effort from Danko Lazovic with his feet.
AEK's hopes were then dealt a terminal blow in the 67th minute when Rosina scored Zenit's second with a shot from the edge of the area that flew into the top-left corner.
Rosina could have had a third soon after when he thrashed a shot over before Blanco's miserable night continued when his header was tipped wide by Malafeev.
It was not to be AEK's night and Denisov sealed a one-sided scoreline when he drilled in a left-footed shot from just outside the area with three minutes remaining.