Rangers fell to a narrow defeat to Hertha Berlin in a friendly clash in La Manga.
Philippe Clement's side couldn't break down the Bundesliga 2 side who had snatched the lead at the end of the first half.
And Rangers played without Clement on the sidelines for much of the second half after the manager was sent off for protesting a decision to penalise Scott Wright instead of awarding him a free-kick.
It was a much-rotated Rangers side in Spain for the winter-break match with two separate XIs sent out before and after the break.
Rangers began with Ross McCrorie, James Tavernier, John Souttar, Leon Balogun, Ridvan Yilmaz, John Lundstram, Nico Raskin, Dujon Sterling, Todd Cantwell, Rabbi Matondo and Fabio Silva.
Rangers started brightly with Rabbi Matondo looking to make the most of an early spell of pressure as he hammered goalwards but Hertha keeper Tjark Ernst beat the ball clear.
Six minutes later and McCrorie was called into action as an awkward bounce in the box forced the keeper into a makeshift clearance to remove the danger.
Matondo again fired towards goal from distance with 24 minutes on the clock but again Ernst was equal to the effort and saved comfortably.
Seconds from the break and Hertha Berlin would snatch a lead in Spain. A corner into the front post found captain Marc-Oliver Kempf who sent a looping header into the far corner leaving McCrorie stranded in the Rangers goal.
After the break, Clement altered his side with Jack Butland, Leon King, Connor Goldson, Johnly Yfeko, Robbie Fraser, Jose Cifuentes, Cole McKinnon, Bailey Rice, Ross McCausland, Scott Wright and Cyriel Dessers starting the second period.
Just seven minutes after the break and Clement was sent off by the match referee after complaining of a free-kick given against Wright who had fallen under pressure from Hertha Berlin defenders.
The referee halted the match after giving a free-kick and produced a red card to Clement for his complaint over the decision.
Just before the hourmark and Wright passed up a major opening. He pinched a loose ball on the edge of the box but could only drag his effort wide of the post.
Five minutes later and Butland was called upon to make a smart stop from Derry Scherhant who had snatched the ball from Goldson.
Dessers would go close with 65 minutes played as his improved effort forced Ernst to beat the ball clear of the goal.
RANGERS XI (first half): McCrorie, Tavernier, Souttar, Balogun, Ridvan, Lundstram, Raskin, Sterling, Cantwell, Matondo, Silva.
RANGERS XI (second half): Butland, King, Goldson, Yfeko, Fraser, Cifuentes, McKinnon, Rice, McCausland, Wright, Dessers.