Monaco earned the first point of their disappointing UEFA Champions League campaign on Wednesday in their first European outing under Thierry Henry.
But their 1-1 draw at Club Brugge still left both sides with little chance of making the knockout stages.
Both Monaco, semi-finalists just two seasons ago, and their Belgian opponents face missing out on the top two places in Group A.
They have both previously lost to Atletico Madrid and Borussia Dortmund in their opening two games.
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In former French international Henry’s second match in charge, the Ligue 1 outfit at least halted their run of five straight defeats.
But they have now gone 12 games without victory since a win at Nantes on the French league season’s opening day.
Struggling Monaco opened the scoring through 18-year-old Moussa Sylla after a 31st minute counter-attack set up by Russian international Aleksandr Golovin’s surging run.
But the lead lasted only eight minutes before Brugge’s Brazilian centre forward Wesley equalised with a header from Hans Vanaken’s cross.
It caught debutant goalkeeper Loic Badiashile out of position.
The 20-year-old was Monaco’s fourth goalkeeper in as many matches as the club battle with an injury crisis.
His absence heightened after midfielder Stevan Jovetic limped off after just nine minutes with a suspected groin injury.
Brugge goalkeeper Karlo Letica made a point-blank stop from Golovin in the 72nd minute.
It helped to keep the score level before the home side’s 18-year-old substitute Lois Openda missed a sitter with virtually the last touch of the match
The two clubs meet again in Monaco on Nov. 6 in their next group game where a place in the Europa League early next year is likely to be at stake.