Arsenal's unbeaten Champions League run in Group H came to an end at Olympiakos after their youngsters were undone by a cool second-half strike by Leonardo.
The Gunners enjoyed much of the possession but Carlos Vela was guilty of wasting two excellent chances.
The hosts livened up after a drab first half, with Leonardo bursting through the defence to slot in the opener.
Lukasz Fabianski denied Leonardo and Kostas Mitroglou while Aaron Ramsey had a late shot cleared off the line.
Olympiakos held on to ensure their progression into the knock-out stages as runners-up.
With Arsenal's top spot assured, boss Arsene Wenger could afford to rest many of his stars, handing a debut to 18-year-old Tom Cruise and partnering reserve-team captain Kyle Bartley with veteran Mikael Silvestre in defence.
The Greek champions needed just a point in Athens to make the final 16, and they began very hesitantly and nervously in front of their noisy supporters.
Arsenal were rarely without the ball in the opening 15 minutes, and fit-again striker Theo Walcott had the first chance but shot straight at keeper Antonis Nikopolidis after linking up well with teenager Jack Wilshere.
Sluggish Olympiakos were restricted to long-range efforts from Luciano Galletti and Dudu thanks largely to Welsh international Ramsey pulling the strings in the absence of rested captain Cesc Fabregas.
The hosts' limp first-half effort was brought to a close rather aptly when defender Raul Bravo blazed a wild volley high and wide.
The second half was a transformation and within five minutes of the re-start Olympiakos were ahead.
Bartley flapped at a tackle on Oscar Gonzalez and the ball fell to Leonardo who strode through on goal and slotted smartly between the legs of Fabianski.
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