Jordan Rhodes scored his first goal for Norwich City but he and his team were beaten 2-1 by Union Berlin in Delbruck.
City undeservedly trailed at the interval after a defensive mix-up allowed Kenny Prince Redondo to nod home.
Rhodes got his first goal in yellow and green on the hour mark after a nice move involving Felix Passlack and Ben Marshall but a Timm Klose own goal moments later meant the German side took the win.
City started with a 4-1-4-1 formation with a back four of Ben Marshall, Timm Klose, Ben Godfrey and Max Aarons in front of Remi Matthews in goal. Louis Thompson played just behind a midfield from right to left of Felix Passlack, Todd Cantwell, Kenny McLean and Teemu Pukki with Jordan Rhodes acting as the lone frontman.
After being on the backfoot for the opening ten minutes, City controlled the first-half and were very patient with the ball, biding their time and waiting for the killer pass.
The closest they came to scoring was on 19 minutes. Pukki chipped the ball wide to Marshall in space on the right-hand side who cut in a picked out Rhodes in the area but his glancing header flashed inches wide of goal.
City continued to dominate possession as the game progressed and went close again on 40 minutes. Passlack stole the ball from a defender but was pulled back - luckily, Pukki raced onto it and was thwarted by the Berlin stopper from close-range.
However, against the run of play, the German side took the lead just before half-time. A mix-up in communication at the back allowed Redondo to steal in, nod the ball over Matthews and into the net.
Daniel Farke was left irate at the half-time whistle after his side were denied an immediate equaliser. Marshall's deep free-kick was bundled in by Godfrey at the back post but was ruled out for apparent handball by the official in the middle, despite no flag from the linesman who was in a better position.
After a quiet start to the second, a moment of quality on the hour mark saw City draw level. Marshall did well to keep his balance under pressure and play in Passlack and his cross was nodded home by Rhodes for his first goal in a City shirt.
However, within minutes, Union Berlin regained the advantage after a long-throw from the right was unfortunately headed over Matthews by Klose and into the corner of the goal.
Farke introduced James Husband, Christoph Zimmermann, Moritz Leitner, Onel Hernandez and Dennis Srbeny in the second-half but Berlin defended well and City were unable to find an equaliser, despite Rhodes going close with a header with five minutes left.