Arsenal 0, Milan 0: Adebayor misses golden chance as Milanese guile stifles Arsenal

Their rivals across town might be the champions of Italy, but no one quite matches the Rossoneri of Milan when it comes to putting ambitious English clubs in their place. Paolo Maldini and friends slammed the door last night on what is supposed to be the greatest attacking force in English football and left Arsenal with the most daunting of tasks at San Siro next month.

As a spectacle, 4 March cannot come quick enough: the night when the arrivistes of Arsène Wenger's new Arsenal team either overthrow the old masters or fail at a familiar hurdle for English clubs. It was supposed to be Internazionale who were coming to England this week to reassert the old hegemony of Serie A but instead it turned out to be Milan, full of the usual suspects like Maldini, Andrea Pirlo and Gennaro Gattuso, who gave a masterclass in the dark arts of Italian football.

It could all have been different in the last moments of injury time when Emmanuel Adebayor headed substitute Theo Walcott's cross against the bar from eight yards out. The Arsenal striker has 22 goals this season yet that one could have been as valuable as any of them. There was no way through a Milan team whose last line of defence was a second-choice goalkeeper who once struggled to get a game at Leicester City. On the night, Zeljko Kalac was safe as houses.

Wenger said that his team are good enough to triumph in Italy against a side who so comprehensively humbled Manchester United in the semi-finals of the Champions League last season. It is evident that it will take a performance on a par with Arsenal's greatest ever away trip to Italy – the 5-1 defeat of Internazionale in November 2003 – to turn this tie around. "With the experience I can say 0-0 is not a bad result," Wenger said. "I didn't dream of 0-0 but not conceding a goal is not a bad result."

Milan, Wenger said, would be favourites for the return leg which is probably just the way the Arsenal manager likes it. Last night his team were undone by an over-reliance on a direct long ball to Adebayor who laboured alone valiantly against first Alessandro Nesta and then, when he retired injured, the peerless Maldini who switched to central defence. At 39 the old-stager is 16 years older than Adebayor but the age showed last night only in the Italian's good judgment.

There will be no Kolo Touré to harness the attacking force of Milan's Brazilians Kaka and Alexandre Pato in San Siro; the Ivorian came off after seven minutes with a calf strain that Wenger said will rule him out for the next three weeks. But there is a more pressing concern for Arsenal and that is that the very best they threw at Milan, the attacking style and verve that has enthralled the rest of the Premier League this season, was just not enough to break down the holders in this competition.

Carlo Ancelotti's Milan are certainly capable of bringing any team down to earth with a bump. On Arsenal's 100th game in the Champions League all those Milan injury doubts were miraculously passed fit and while Pirlo and Clarence Seedorf were not the dominant figures they were against United in the semi-final last season they managed to disrupt what fluency Arsenal had. But for a 10-minute blitz in the opening stage of the second half, Wenger's side never quite found their stride.

Other than when Liverpool broke the law of football logic in the Champions League final of 2005, English clubs encounter a mental block when it comes to breaking down Ancelotti's 4-3-2-1 formation. They find the midfield too congested; the defence as willing to scrap as any in the Premier League. Milan have a habit of sapping the strength and momentum from any team, already Wenger was muttering about the dire state of the pitch at San Siro last night but that will be the least of his worries.

There were only flashes last night of what Kaka and Pato can produce but it was enough to concern Wenger that both could run riot in the second leg. Unusually Philippe Senderos, on in the place of Touré, looked solid but will he be able to repeat the feat when Kaka is on home territory next month? Wenger will expect more from Eduardo da Silva than the Croat delivered last night but, as Cristiano Ronaldo will confirm, away games at Milan can make even the most prodigious talents retreat into their shells.

Back to that 10-minute spell when Arsenal had Milan on the rack shortly after Nesta's injury. The architects of the most brilliant raids were Alexander Hleb and Cesc Fabregas who, in that brief spell, passed the ball through spaces in the Milan defence that the Italians did not seem to be aware existed. The pick of these early moves was a spectacular sweeping affair in the 52nd minute that shaped up to be the best goal of Arsenal's season.

From his own half, Fabregas found Eduardo, from there possession went out wide to Hleb and, breaking in from the touchline, the winger cut the ball back to Emmanuel Eboué. Half the pitch had been covered in a matter of seconds and Eboué was presented with the ball just inside the Milan box. He should have done much better than shoot wide.

Eventually Milan weathered the very best that Arsenal had to throw at them and did not look stretched until the very last moments of the match. Wenger sent on Nicklas Bendtner in place of the peripheral Eduardo and the Dane had one chance but smashed it over the bar. Adebayor missed in the penultimate move of the match and the realization dawned that Arsenal have an exacting task in 13 days' time.