Rangers have crashed out of the Europa League after suffering a 2-0 defeat away to Progres Niederkorn of Luxembourg - the tie finished 2-1 on aggregate.
Progres only finished fourth in the Luxembourg National Division last season and their victory against the Scottish giants was their very first one in European competition.
During the game, Rangers only registered 3 shots on target as they ultimately fell to goals from Françoise and a 75th minute free-kick from Sébastien Thill.
Prior to tonight, the Luxembourg side had only ever scored one goal in European competition, but they advance to play AEL Limassol or St Joseph's in the next round.
It was only nine years ago that Rangers reached the UEFA Cup final, losing to Zenit Saint Petersburg in Manchester, but this latest defeat is surely one of the darkest moments in the club's history.
Pedro Caixinha's men start their league campaign away to Motherwell on August 5th.
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