A controversial late own goal condemned Rangers to a Champions League second round defeat against Benfica and left their group stage hopes on a knife edge.
Two goals from Kayla McCoy looked to have sealed the tie to take the Scottish champions to Lisbon.
But Benfica secured victory when goalkeeper Victoria Esson was adjudged to have taken the ball narrowly off her line following a nasty deflection.
Ana Vitoria equalized and then put Benfica ahead in a thrilling match.
The sides meet again next Wednesday, with Rangers still level despite a late heartbreak.
Ibrox has seen some of Europe’s biggest nights in the past. For Rangers Women, it was arguably the biggest tie in their history, and their first Champions League game on home soil.
However, they looked nervous at the start and Benfica, the Portuguese champions, should have taken the lead after 19 minutes when an unmarked Marta Cintra headed home at the far post.
Rangers weathered the storm and struck first when Brogan Hay picked out McCoy, who beat goalkeeper Rute Costa with a low header at the near post.
And as the hosts’ nerves began to fray, Jenny Danielsson should have done better than shoot straight at Costa when she was left alone outside the box.
But Rangers were caught napping, from his spot-kick, as Benfica stole possession and Vitoria played a one-two before driving inside the box and clinically finishing the far corner.
After the break, Benfica started to show their quality again and the Gasteiz player scored the second goal in the roof of the net, between Esson’s beautiful saves, to deny Pauleta twice.
However, Rangers found an equalizer just two minutes after falling behind when McCoy latched on to Nicola Docherty’s long ball and fired home a left-footed shot.
Benfica remained unconvinced and continued to up the tempo, eventually finding a third in strange circumstances when Esson had to step back to stop Lisa Martinez’s attempted header.
Rangers were adamant that their goalkeeper had let the ball cross the line, but the assistant referee awarded the goal and Benfica saw the game out.
Rangers leave everything to do in Portugal and the deficit could have been bigger, but Lucia Alves hit the bar late on when she let fly from 25 yards.
Man of the Match – Brogan Hay
Against the Rangers, but prove their courage – analysis
History was going to be made regardless of the score. As Rangers, as champions in Scotland, played their Champions League tie at Ibrox, it measures their progress and Scottish women’s football.
But the bar continues to rise, and now Rangers have been given the chance to mix with Europe’s elite in the group stage.
At times Benfica, who reached the group stage for the first time last season, looked a quality outfit and passed the ball around, and certainly created the better chances.
The second game showed that the task ahead of Rangers is huge, but they were clinical when they got their chances and showed they have the players to compete at this level.
Rangers host Motherwell in the Scottish Women’s Premier League on Sunday (4pm BST), then travel to Lisbon to face Benfica in the first leg of the Champions League on Wednesday (7.30pm BST).
- 7Heyreplaced byOrschmannin 74′minutesBooked in 90 minutes
- 18the cornet
- 6In the afternoon
- 23MacLeanreplaced byWatsonin 71′minutes
- 20Danielssonreplaced byArnotin 61′minutes
- 10McCoyreplaced byhowin 74′minutes
- 30the gray
- 66Coastal Fields
- 3Silva Seiça
- 15it’s Silva Costa
- 71da Silvareplaced bySilva Sobrinhoin 45′minutes
- 13Sousa Alves
- 21Dominguez Encinas
- 6Martins Fariareplaced byBlackin 90+2′minutes
- 8is Silva Cintrareplaced byManjenje Nogueira Silvain 83′minutes
- 10Kliemaschewsk de Araújo
- 7Cantuário da Silva
- 14Costa Malheiro Dias Correia
- 28Silva Sobrinho
- 29Sá Pessoa by Brás Nogueira
- 33the golden
- 39bad days
- 77Manjenje Nogueira Silva
- Ivana Martincic