Manchester City Women suffered an agonising defeat to Real Madrid to crash out of the Champions League.
Claudia Zornoza’s first-half goal sent Madrid through to the group stage 2-1 on aggregate after a 1-0 win at the Academy Stadium.
Hayley Raso hit the bar and Ellen White had a header cleared off the line as City dominated much of the game.
After a 1-1 draw in the first leg in Spain, City, who reached the quarter-finals last season, looked for an early goal and Steph Houghton headed wide from a corner.
The hosts were the better side but almost fell behind when Nahikari Garcia steered in after squeezing clear, only to be denied by the offside flag.
But Madrid grabbed the lead on the night and on aggregate just before the break when City failed to clear a corner which fell to an unmarked Zornoza and she drilled in a deflected effort beyond Karima Taieb.
The hosts should have levelled 11 minutes into the second half when White seized on a Madrid mistake and squared to Caroline Weir but the Scotland international failed to make contact with the goal gaping.
Nine minutes later, City again came closer to a leveller when Raso wriggled into the box before hitting the bar.
The hosts continued to dominate and White’s header was cleared off the line with 11 minutes left but they could not final a leveller to force extra-time.