Manchester City’s hopes of reaching the group stage of the Women’s Champions League were sunk by former player Caroline Weir.
Weir scored the only goal of the game to give her new side Real Madrid a 1-0 victory in an entertaining contest at the Estadio Alfredo Di Stefano.
The 27-year-old Scotland international struck in the 15th minute, brilliantly controlling a cross and turning her marker before lashing a left-footed shot into the top corner.
Weir was also not far away with an audacious 40-yard lob a few minutes later and team-mate Kathellen Sousa somehow contrived to hit the bar with a header from three yards out, but City also had chances to equalise through Laia Aleixandri, Vicky Losada and Bunny Shaw.
Gareth Taylor’s side were unable to get back on level terms and also suffered a worrying injury to England’s Euro 2022 final heroine Chloe Kelly, who was forced off early in the second half.
Rangers had earlier progressed to the next round with a 4-0 win over PAOK, captain Nicola Docherty opening the scoring and Hannah Davison and Lizzie Arnot also on target either side of an own goal.
Glentoran and Glasgow City finished bottom of their groups after both lost on Sunday, Glentoran beaten 2-1 by Maltese champions Birkirkara and Glasgow losing 1-0 to Swiss side Servette.
Shelbourne also bowed out of the competition after losing 3-0 to Icelandic side Valur, with goalkeeper Amanda Budden sent off for two bookable offences in stoppage time.
Swansea, meanwhile, head into their Genero Adran Premier title defence on the back of a humbling defeat after Ferencvaros cruised to a 7-0 triumph in Katerini.