West Ham United's Development Squad were edged out 2-0 by German side Freiburg in their opening match at the VTB Lev Yashin Cup in Moscow.
Ian Hendon's Hammers travelled to the Russian capital on Wednesday before attending the opening ceremony for the six-team Under-21 tournament the following afternoon.
The ceremony included a performance from group 'Dynamite' and a welcome speech from host club Dynamo Moscow's executive director Alexander Borodyuk.
It was then down to action at the Luzhniki Olympic Complex, where West Ham were on level terms at half-time against their opponents, and could even have been ahead had a convincing penalty shout gone the Hammers' way.
The second half was a different story, however, as Freiburg scored once before netting a penalty of their own to take a match-winning lead. There was still time for Jake Larkins to save a spot-kick, but West Ham could not find a way back into the game.
Aside from the impressive Larkins, defender Declan Hunt made his first appearance in a year after recovering from a serious knee ligament injury, while winger Dominic Vose injected some energy when he appeared as a substitute.
Hendon admitted his team had been second-best against Freiburg, but pointed to the fact that the Germans are two weeks ahead of the Hammers in terms of pre-season preparations.
"It was our first game and we were a little bit rusty, as is to be expected," said the coach. "Freiburg had been back in training for two weeks and it showed a little bit.
"One bonus was that there was a small group of Russian West Ham fans at the game and they were singing their songs and giving us some good support. They even got themselves on the TV!
"We will re-group and be ready for Dynamo Moscow on Friday, but they will be fresh as they didn't play on Thursday and this will be their first match. I'll give a few of the older boys like Pelly Ruddock and Eoin Wearen a rest as they played at Boreham Wood on Tuesday night and againt on Thursday.
"Whatever happens, it is a good experience for the young players to be playing foreign teams and travelling so far from home. I had never been to Russia myself before so it's been a learning curve for all of us and we're enjoying it."
Captain Wearen told whufc.com the Hammers hoped to return to winning ways and produce a better performance when they take on host club Dynamo Moscow on Friday evening.
"We didn't play great, to be fair," said the Irishman. "They were a good side but things didn't exactly go our way! We conceded two goals straight after half-time which killed us.
"We had a few chances and should have had a penalty in first half but our concentration let us down at times.
"So, it's on to the next one on Friday. Hopefully we can do ourselves justice then."
In Thursday's other opening group-stage matches, the Mexico Under-20 national team scored six second-half goals to beat Turkish side Besiktas 7-0.
Friday will also see Spanish side Malaga enter the tournament. The final and third and fifth-place matches will take place on Sunday.
West Ham United Development Squad: Larkins, Driver, Shaw, Moncur, Wearen, K.Lee, Ruddock, Powell, McCallum, Turgot, Fanimo
Subs: Baxter, Hunt, Seidu, Chambers, Sadlier, Alexander, Miles, Vose