Olympiakos secured their place in the last 16 of the UEFA Champions League after claiming a narrow victory against a youthful and very much watered-down Arsenal side.
One point was all Olympiakos needed against the already qualified English side.
APOEL of Cyprus meanwhile, were knocked out of the Champions League despite claiming a 2-2 draw away to Chelsea at Stamford Bridge.
Olympiakos 1 Arsenal (ENG) 0
Leonardo struck the only goal of the game two minutes after half-time as the Greek champions ensured a first knockout round place as Group H runners-up behind Arsene Wenger’s side.
Having already clinched top spot, the Arsenal manager fielded a starting lineup with an average age of just 21, but they were unlucky not to snatch at least a draw with Carlos Vela coming close twice.
Zico had stressed in advance the need for Olympiakos not to simply look for the draw they required, but it was the visitors, with Theo Walcott full of running, who controlled much of the early possession as the home team made a nervous start.
Moving the ball around confidently, it took Arsenal just ten minutes to register the first effort on goal, Walcott stinging the palms of Antonis Nikopolidis with a sharp shot from inside the penalty area.
Kostas Mitroglou responded three minutes later, slicing an effort over the crossbar.
Arsenal were then presented with a chance to take the lead when Olof Mellberg felled Vela just outside the box, but Walcott smashed his free-kick straight into the defensive wall.
The Greek champions then broke and Luciano Galletti volleyed Leonardo’s cross into the side-netting.
Arsenal continued to control the midfield, however, and Walcott, back in the team after a hamstring injury, was proving a constant threat in and around the penalty area with his quick feet and darting runs.
Galletti was Olympiakos’ main outlet down the right and the Argentinean gave left-back Thomas Cruise a difficult Arsenal debut.
The visitors kept their hosts at arm’s length, though, and it took Mitroglou 43 minutes to register Olympiakos’ first shot on target with a speculative effort which Lukasz Fabianski gathered comfortably.
Shots followed from both Dudu and Raul Bravo as Olympiakos pressed forward, both sailing over the crossbar.
The second half began with a flourish when Olympiakos took the lead two minutes in. Arsenal were caught cold when the ball broke kindly for Leonardo in midfield and the Brazilian winger surged into the penalty area before slotting through the legs of Fabianski.
Frenzied celebrations ensued as the home fans sensed the first knockout round was near, although they had cause to be thankful just four minutes later when Vela burst through and only a brilliant Nikopolidis save kept his team ahead.
Walcott curled a free-kick just round the right post as the Gunners stepped up the pressure and Vela prodded over with only Nikopolidis to beat in the 70th minute.
At the other end, Leonardo was denied by Fabianski’s sprawling save after being played in by Dudu and the visiting goalkeeper then got the faintest of touches to direct a Mitroglou effort wide.
Arsenal pressed forward in the closing stages as they sought an equaliser but Nikopolidis put in several good blocks to secure a third home win in the group and with it a place in the last 16.
Chelsea (ENG) 2 APOEL (CYP) 2
Cypriots APOEL ended Chelsea run of ten matches without conceding at Stamford Bridge and then repeated the trick with three minutes remaining to earn a surprise draw.
It was not enough to propel the Cypriot side into the UEFA Europa League but the memory of how they stood up to one of the continent’s dominant forces – albeit a side missing several first-choice players – will live with them for a long time.
Marcin Zewlakow’s early strike was overturned before half-time as Michael Essien and Didier Drogba got on the scoresheet.
Chelsea continued to dominate and always looked the likely winners but they were rocked when, three minutes from time, substitute Nenad Mirosavljevic stole in for the equaliser.
Carlo Ancelotti gave UEFA Champions League debuts to goalkeeper Ross Turnbull and Gael Kakuta and the former was quickly called into action, plunging to his right to beat away Joost Broerse’s shot on the turn after a cleverly-worked free-kick.
It was a stark warning to Chelsea’s rearguard, but not heeded as Zewlakow became the first player to breach them at home in eleven matches.
Konstantinos Charalambides found enough time and space to engineer a pass for the Polish striker to stride on to and easily beat the onrushing Turnbull.
It silenced much of Stamford Bridge while the 5,000-strong APOEL supporters let their surprise and delight be heard.
The home fans were soon rising to cheer a Joe Cole header which flashed into the net following Florent Malouda’s precise cross only for the offside flag to rule it out.
Nevertheless, the shock of falling behind served to concentrate Chelsea minds and they were pouring forward in droves.
The equaliser followed another well-constructed incursion into the heart of the visitors’ defence with Essien taking possession before side-stepping his man and unleashing a firm drive which Dionisios Chiotis could not keep out.
Essien limped off shortly after but with Frank Lampard taking over there was unlikely to be any interruption to Chelsea’s supremacy.
Almost immediately Yuri Zhirkov advanced to find a crossing position down the left. Drogba pulled away from his markers and there was room aplenty to drive in the second.
There was nothing at the start of the second half to suggest the balance of play was about to witness a significant change.
Cole came close to Kakuta’s low delivery while from a promising position Drogba sensed an opportunity to add to his recent tally of free-kick goals but aimed narrowly wide.
As the rain continued to pour down and Chelsea remained camped in the APOEL half, it seemed the only relevant issue was how many goals the home side would be satisfied with.
Cole bounced a long cross off the crossbar but the look on his face was a giveaway that his intention had been to find a team-mate rather than go for goal. Terry had a goal ruled out and was then found wanting at the other end as Chelsea gave the ball away and Mirosavljevic pounced to deliver the visitors a point.