Olympiakos 2-1 West Ham: Kostas Fortounis strike and Angelo Ogbonna own goal consign Irons to defeat
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Olympiakos were without a win in their past six home games against English clubs in major European competitions (D2 L4) since beating Manchester United 2-0 in the Champions League in February 2014
West Ham slipped to their first Europa League defeat of the season as they were narrowly beaten at Olympiakos.
Kostas Fortounis surged through the West Ham defence and struck from 25 yards to open the scoring.
Angelo Ogbonna then turned into his own net just before the break to further deflate the Irons.
Lucas Paqueta's brilliant volley in the 87th minute came too late with the Hammers unable to salvage something from the game.
David Moyes' side remain top of Group A despite losing.
Olympiakos started brightly, Sotiris Alexandropoulos' early effort forcing Alphonse Areola to save low down to his left.
The home side were winless in their past 11 Europa League games, their longest run without victory in major European competition, but there was no lack of confidence against West Ham.
The Hammers dominated possession but looked disjointed throughout, with Said Benrahma firing against the side-netting in the early stages.
James Ward-Prowse whipped a promising free-kick wide of the post, while Danny Ings got on the end of a corner but could not keep his header down and it nestled on the roof of the net.
Irons' European unbeaten record ends frustratingly
West Ham became the first English side to go 17 consecutive games in European competition without defeat when they won at Freiburg this month.
However, they looked lacklustre from the start in Greece with seven changes made from the team that lost 4-1 at Aston Villa on Sunday.
"Look, we changed a lot of players tonight, we've got the Premier League coming up and we've got a League Cup game next week and we'd won the first two games in the group, which gave us leeway to make changes tonight," Moyes told whufc.com.
"I don't think anybody could say the team we started with wasn't a good team and wasn't a team capable of winning or performing.
"Many of them have been very good players for us over the years and still are."
Buoyed by a raucous home crowd, Olympiakos were on the front foot from the outset and had two early corners to show their intent.
Poor defending was to blame for both first-half goals, Konstantinos Mavropanos affording Fortounis space, whose brilliant individual effort was struck home from the edge of the box.
Ogbonna then flicked his leg at the ball following a hopeful cross swung in by Rodinei as West Ham conceded two goals in the last 15 minutes of the first half.
Paqueta halved the deficit with a superb left-footed volley into the bottom corner after Michail Antonio's cross was only half cleared, but it was too little, too late as Moyes' side were made to pay for an ineffectual display away from home.
This was just West Ham's second group-stage defeat in nine such matches, and they will look to get back to winning ways when they host Olympiakos on November 9.