James Norwood netted his first goal for the Blues but couldn't prevent Town from falling to a 4-1 defeat to Fortuna Düsseldorf in their opening 45-minute game at the Interwetten Cup in Meppen.
Norwood was starting his first game since his summer move from Tranmere having started pre-season late.
Fortuna began the game on the front foot and threatened early on from a corner which Town repeatedly failed to clear.
Then in only the third minute the Bundesliga side took the lead. Mattheus Zimmermann crossed from the right and skipper Oliver Fink flicked a header across Bartosz Bialkowski and into the corner of the net.
However, from the kick-off the Blues levelled. The ball was played through to Norwood who found himself in on goal and the striker deftly beat the advancing Michael Rensing to claim his first goal in a Town shirt.
The former Tranmere man had another opportunity in the sixth minute, winning a challenge on the edge of the box which saw him through once again but this time Rensing blocked. The rebound flew out to Armando Dobra, playing on the left side of Town’s 4-1-4-1 system, but the ball struck the youngster’s hand.
Norwood was clearly relishing his return to action with his battle with centre-half Alfredo Morales leading to an ongoing exchange of views between the pair with the striker feeling he had pulled back when he had his second chance.
The German side regained the lead in the 10th minute when Erik Thommy struck a speculative shot from distance which somehow squirmed under Bartosz Bialkowski.
Fortuna made it 3-1 in the 14th minute when Bernard Tekpetey pacily burst away down the right following a Town freekick in the Fortuna half leaving a number of Blues players in his wake and cut the ball to his left to Thommy, who turned in his second of the game from close range.
Town lost centre-half Toto Nsiala to what looked to be a pulled hamstring following the third goal with Bailey Clements coming on at left-back, Tristan Nydam moving into midfield and Cole Skuse from the holding midfield role into the centre of the defence.
Fortuna increased their lead in the 27th minute when Zimmermann crossed from the right of the box, Emyr Huws scuffed his clearance and the ball fell to Tekpetey, who finished clinically.
The German side dominated having established such a commanding lead and went close again in the 33rd minute when Thommy shot not too far wide from the left.
Two minutes later, the Norwood and Morales spat continued with the striker feeling the Fortuna man had elbowed him. Norwood shoved the Fortuna midfielder in the aftermath and both were yellow-carded. A minute later, sub Clements joined them in the book for a foul on Tekpetey.
In the final scheduled minute Nydam was caught in possession on halfway, Thommy broke forward and slipped the ball across Bialkowski towards waiting team-mates but Woolfenden turned it behind.
Seconds before the whistle Nydam was caught by a very well-struck shot in his groin from point blank - leading to painful reactions in sympathy from around the ground - and was receiving treatment as the rest of the players left the pitch.
No disgrace in losing to a side which finished 10th in the Bundesliga last season, however, manager Paul Lambert will be disappointed in the manner of some of the goals.
The Blues’ approach of passing the ball out from the back again played them into trouble on a number of occasions and they failed to cut out crosses from the right in particular on a number of occasions.
The Blues were never really able to impose themselves on their more lauded opposition, although played it around neatly at times, if largely unthreateningly.
Norwood took his goal confidently and will feel he might well have added a second had he not been pulled back when he had his later opportunity.
Town will now sit out while hosts SV Meppen take on Dutch Eredivisie side FC Utrecht for a place in the final. Town will face the losers in the third-fourth play-off in just over an hour’s time.
Town: Bialkowski, Donacien, Nsiala (Clements 16), Woolfenden, Nydam, Skuse, El Mizouni, Huws, Lankester, Dobra, Norwood.
Fortuna: Rensing, Ayhan, Morales, Fink (c), Barkok, Thommy, Giesselmann, Hennings, Bormuth, Tekpetey.