And this latest set-back will surely have piled even more pressure on under-fire Milan coach Leonardo.
In four home matches this season Milan have scored only one goal, also winning only once, while they have fared little better on their travels.
But the significance of this home defeat to European football minnows can hardly be understated, particularly as Milan's next two Group C games will be against free-scoring Real Madrid.
And Leonardo admitted his team have lost a certain aura.
"We're struggling to do what we want to do, we have the desire but we're not managing to do it.
"If you think about today, our performances and our results won't be putting fear into the rest of the world.
"But don't forget we beat Marseille 2-1 and with the same team. I believe in this team and I believe we have the resources to get out of this situation."
Having also won only two of six league matches, already Milan's pretentions both at home and in Europe look decidedly fragile.
Leonardo began this game under pressure and the first half would have made uncomfortable viewing for the Brazilian.
Zurich coach Bernard Challandes admitted his team had at times been under the cosh but said they deserved their result.
"It's clear that we're very, very happy to have beaten Milan away from home, it's an historic victory for us," he said.
"We're a small team and we've won away to Milan. In the last few years we talked about commitment and we got a lot of that tonight.
"Lately results haven't been what they should be, so I'm proud but we were also a little bit lucky.
"We needed that because in the second half Milan put us under a lot of pressure, we had a bit of luck but that shouldn't deflect from the team's credit because they deserved it."
On seven minutes Milan full-back Ignazio Abate mishit a cross from the right that almost caught out Zurich goalkeeper Johnny Leoni, who bizarrely reacted by kicking the ball off his line.
But on 10 minutes the visitors were in front with a goal from a former West Ham player that the Premier League club's current manager would have been proud of.
Milan Gajic swing over a corner and Tihinen arrived unmolested at the near post to flick the ball with his heel between his legs and past Marco Storari in the Milan goal -- a near copy of a goal Hammers boss Gianfranco Zola scored for Chelsea against Norwich in 2002.
It was an open game and after Clarence Seedorf had volleyed over for the hosts, Johan Volanthen escaped on the counter-attack and pulled the ball back for Xavier Margairaz, who failed to keep either his shot or his head down.
Leonardo wasted no time in trying to fire up his side, bringing on former world player of the year Ronaldinho for Seedorf at the break.
Just before the hour mark Inzaghi almost levelled again as he met a dangerous Andrea Pirlo free-kick with his head but Leoni made a flying one-handed save.
Moments later Ronaldinho sent Pato in on goal with a sumptuous through ball but although his young compatriot lifted the ball over Leoni, it dropped wide of the post.
Leoni then blocked a close range Inzaghi shot with his foot and Storari kept out a drilled Margairaz effort with his boot.
Milan kept pushing and on 88 minutes captain Massimo Ambrosini shaved the outside of the post with a low strike from 20 yards.
With almost the last kick of the match Gianluca Zambrotta crashed a stunning shot against the Zurich upright but the Swiss deserved that bit of luck and the three points to boost their qualification hopes after their 5-2 home defeat to Real.
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