Arsenal contrived to miss a hatful of clear-cut chances as they eventually had to settle for a point in an entertaining goalless draw with CSKA Moscow at the Emirates Stadium.
But with FC Porto winning in Hamburg, Arsene Wenger's side now face a battle to qualify for the last 16 of the Champions League from Group G.
After losing 1-0 in the Russian capital two weeks ago, the Gunners needed to hit back by gaining a three-point haul on home soil but, despite producing some scintillating football, they failed to find the target and missed some gilt-edged chances in the process.
Wenger's side were completely on top in the first half and could easily have led by six goals at the interval.
Robin van Persie wasted two early chances before Thierry Henry clipped a 17th-minute effort wide after great inter-play between Tomas Rosicky and Gilberto Silva - he should have scored.
Ten minutes later Cesc Fabregas played a neat one-two with Rosicky and rounded CSKA keeper Igor Akinfeev but somehow managed to fire his shot into the side-netting with the goal gaping.
Worse was to follow for Arsenal as, in the 35th minute, van Persie stabbed a shot past Akinfeev but also wide of the goal before Rosicky contrived to side-foot the ball to the CSKA keeper from three yards out with the most open of open goals beckoning. It rivalled Fabregas' effort for miss of the season.
Wenger's side lost their way after the interval although they still had chances to win the encounter.
However, CSKA also had their opportunities particularly when the lively Vagner Love barged his way into the penalty area in the 57th minute. The under-worked Jens Lehmann half-saved the Brazilian's shot and crawled back towards his goal-line before falling on the ball.
Four minutes later van Persie's cross was just too far ahead of Fabregas before Henry looked certain to score only for his chipped shot to drift past the post as van Persie just failed to get a toe on the ball.
With 16 minutes left the young Dutch striker headed inches wide with Akinfeev stranded before the Russian keeper was forced to make his only outstanding save of the evening - a great one-handed effort to keep Gilberto's goalbound header out.
As Arsenal ran out of ideas in the closing stages, there was almost a dramatic late Henry goal as the Frenchman almost put the ball in his own net - but a CSKA goal would have been just too cruel on the misfiring Gunners.