Barcelona's perfect Champions League record ends with 1-0 loss to Shakhtar Donetsk

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Barcelona missed its chance to reach the knockout rounds of the Champions League with games to spare after a 1-0 loss to Shakhtar Donetsk on Tuesday.

A draw would have been enough to secure Barcelona a spot in the round of 16 for the first time after two straight eliminations in the group stage of Europe's top club competition.

The result ended Barcelona's perfect Champions League record this season and moved Shakhtar into position to also advance from Group H.

Barcelona has nine points from its first four matches, three points more than both Shakhtar and Porto, which hosts winless Antwerp in the other group match later Tuesday.

Danylo Sikan scored the winner with a header in the 40th minute in the game that Shakhtar hosted in Hamburg, Germany, because of the war in Ukraine.

Shakhtar is making its seventh consecutive group-stage appearance but failed to reach the knockout rounds in the last five seasons. It had won only three of its last 20 matches in European competitions.

Barcelona had lost only once this season — to Real Madrid in the Spanish league "clasico" last month. It had no attempts on target through the first hour in Hamburg.

Barcelona had beaten Shakhtar 2-1 at home in the previous round.

Shakhtar forward Newerton made his first Champions League start. The teenager had a goal disallowed for offside in the 87th.

Reporting by The Associated Press.