Ally McCoist suffered defeat in his first 90 minutes as Rangers manager as the Scottish champions lost to German minnows Sportfreunde Lotte in their opening pre-season match.
An experienced Rangers team drew a blank in the opening 45 minutes in the Solar-Technics Arena in Lotte, North Rhine-Westphalia.
But a much-changed outfit conceded just after the break and Rangers could not haul back the team from Regionalliga West, one of three regional divisions underneath the third tier of German football.
The lively Kane Hemmings came close on several occasions and David Healy missed a good late chance.
Rangers included Juan Manuel Ortiz in their starting line-up following the Spanish midfielder's signing from Almeria little more than 24 hours earlier.
David Weir captained the team despite the 41-year-old technically being a free agent following the expiry of his contract at the end of last season.
Kirk Broadfoot was also named in the starting line-up as he continues to recover from a lengthy foot injury.
An early cross from Gregg Wylde caused problems but the home side had the first effort on goal when Martin Hess broke clear, but he shot well wide.
Steven Naismith was wide with an overhead kick for Rangers before Lee McCulloch and Nikica Jelavic came closer from long range for the visitors.
Rangers continued to dominate possession, with Naismith having a goal ruled offside just before the interval.
McCoist made seven changes at the break with youngsters Hemmings, Salim Kerkar, Jordan McMillan, John Fleck and Kyle Hutton among those coming on.
Another substitute, Healy, came close from a tight angle before the hosts took the lead in the 52nd minute, when Simon Engelmann cushioned a volley past replacement goalkeeper Neil Alexander at the far post.
Norwegian youngster Thomas Kind Bendiksen came on as Rangers took time to settle after the goal but Broadfoot came close with a header midway through the half.
Hemmings forced a good save after a clever run before the German side's substitute goalkeeper almost punched Kerkar's cross into his own net.
Rangers stepped up a gear and Hemmings fired just wide before Healy glanced a header wide after being set up well by Wylde with 10 minutes left.
The Northern Ireland striker's miss proved to be the best chance the Light Blues would have as they ran out of steam in the closing stages.
McCoist's men will be looking for a better result when they face Bochum on Saturday.
Rangers first-team coach Ian Durrant preferred not to read too much into the result, saying after the game: "The boys are still bedding in and they've still to get to the fitness levels they want to reach.
"We've taken this game on early and I think you can see there is still a bit of rustiness there. But we will get the opportunity to work on the training ground now and we will be ready for the next two games.
"We now have a good test against Bochum to look forward to and Leverkusen next week. All the boys will get minutes on the park but with it being our first game tonight there was wee silly mistakes here and there.
"But again we can't look too much into this result although the boss will be looking for a reaction when we take on Bochum."
Regarding new arrival Ortiz, Durrant said on the official Rangers website: "Juan is short of fitness and he's only had two days with the boys, he's still getting to know them, but he is going to be a great addition and it was nice to see Kirk Broadfoot and Lee McCulloch on the pitch again. They are important to our squad."