Celtic's poor away record in Europe continued as they lost 1-0 to ten-man Anderlecht in Brussels sending them to the bottom of Group A.
A lack-lustre Celtic side failed to contain the Belgians' strikeforce led by prolific striker Aruna Dindane and eventually succumbed in the 72nd minute leaving themselves with a difficult route to the next round of the competition.
Both sides took their time to settle into the match but Anderlecht found their stride quicker than the visitors.
John Hartson and Stilian Petrov were penalised early on as they struggled to contain the Anderlecht strike force.
Aruna Dindane was proving particularly difficult to mark as he ran riot in the Celtic half while Ivica Mornar was also creating chances for the Belgian side.
Chris Sutton, back in the Celtic starting line-up after injury, had the visitors best early chance but pushed his shot wide of Daniel Zitka's goal.
With 15 minutes gone Anderlecht were in control of the possession and showing more fluency in their play than the Glasgow side.
But just as they looked to be overwhelming the visitors, captain Glen de Boeck was booked for a challenge on Henrik Larsson. And less than ten minutes later de Boeck was expelled from the game after receiving a second yellow card for a heavy challenge on Hartson.
Celtic took advantage of their one-man advantage with Larsson and Sutton pushing forward and creating chances, but neither man could convert their attempts on goal and Anderlecht held on to go into the interval level with the visitors.
Despite their one-man disadvantage Anderlecht showed no signs of caving in. Mornar and Dindane continued to cause problems for the Celtic defence and the visitors could not convert their opportunities in front of goal.
The worst offender was Stanislav Varga who missed when unmarked and just three yards out from goal.
Celtic were left to rue their missed opportunities when Anderlecht took the lead on 72 minutes.
A Bobo Balde header fell at the feet of Christian Wilhelmsson who found Dindane on the edge of the area.
The Ivory Coast international beat Magnus Hedman to score his ninth goal for Anderlecht.
A tired-looking Celtic side could not fight their way back into the game and if anything Anderlecht looked the more likely to extend their lead with Hedman having to make a good save from a Dindane shot in the final minute.