Rangers look set to miss out on the Champions League after suffering a 3-1 home loss to Club Brugge in the first leg of their play-off tie on Tuesday.
The Scottish side made a disastrous start as a defensive mix-up allowed Romeo Vermant to run through and loft the ball over goalkeeper Jack Butland from 30 yards.
Defender Jorne Spileers swept in a corner as Brugge doubled their lead inside seven minutes at Ibrox.
The bitter mood inside the ground soured further when centre-back Brandon Mechele blasted in a third from just outside the area on 20 minutes.
Danilo pulled a goal back at the start of the second half but Rangers have a huge task on their hands going into next week's return leg in Belgium.
Qarabag of Azerbaijan won 3-1 against Ferencvaros in Hungary to take a big step towards the league phase, with Cypriot side Pafos 2-1 winners at Red Star Belgrade.
