Irish Premiership side Crusaders frustrated Premier League club Wolves, before a cruel late goal saw them lose 2-0 at Molineux.
Striker Jota scored the hosts first goal in Europe for 14,176 days to put Wolves on course for victory in their Europa League second qualifying round first-leg tie at Molineux.
Vinagre's injury-time goal, after goalkeeper Sean O'Neill's mistake, then added breathing space for dominant Wolves ahead of next week's second leg in Belfast.
Morgan Gibbs-White and Leander Dendoncker went close while Jota could have added to his tally but Nuno Espirito Santo's side were frustrated by the plucky visitors for long spells.
Crusaders will take heart from their display at Molineux, where they refused to roll over, but Vinagre's goal is likely to have put the tie out of reach.
Rangers hope a 2-0 lead will be enough to exorcise the Europa League ghosts of 2017 after missing the chance to kill off old foes Progres Niederkorn at the first attempt.
The part-timers from Luxembourg dished out one of the biggest upsets in Gers' history when they dumped Pedro Caixinha's side out of the competition two years ago.
Goals from Joe Aribo and on-loan Liverpool youngster Sheyi Ojo at Ibrox mean Steven Gerrard's men should now go on and bury those painful memories.
Meanwhile, a penalty for Sam Cosgrove rescued a draw for Aberdeen against Chikhura Sachkhere in Tbilisi.
