Rangers will play in the Europa League group stage after losing out to PSV Eindhoven in the second leg of their UEFA Champions League Play-off.
The tie was evenly poised at 2-2 following the first leg at Ibrox but PSV ran out 5-1 winners in Eindhoven to progress 7-3 on aggregate.
Ismael Saibari scored twice to put the Dutch side in control before James Tavernier pulled one back just after the hour mark.
Luuk De Jong restored PSV's two-goal lead on the night before a Joey Veerman effort and an own goal from Connor Goldson put the match beyond Rangers' reach.