It was billed as the clash between young and old, the grand masters of European football versus the new pretenders. But after 90 exhausting yet goalless minutes at the Emirates, we are still no nearer to knowing just who will be taking their place in the last eight.

AC Milan will be the happier side with the result of course, a clean sheet away from home is pleasing in any game, let alone one against a side that had already managed fifteen goals in their previous four home matches in this season’s competition, and having seen their first choice keeper (Dida) ruled out entirely, then their main centre half (Alessandro Nesta) forced off just five minutes into the second half, the achievement is all the more impressive, and may well give them the all important advantage in the tie.

For Arsenal it was a night of frustration, compounded by Emmanuel Adebayor heading against the crossbar in front of an open goal in stoppage time, and they will need to succeed where Manchester Utd failed last season by getting a result in the San Siro in a fortnight’s time. Perhaps crucially, they will need to do this without the influential Kolo Tourè, who lasted just seven minutes before succumbing to a calf injury which looks set to keep him out for “three or four weeks” according to Arsene Wenger. And whilst Philippe Senderos was faultless as the Ivorian’s replacement, it is an injury headache Wenger could well do without at such a crucial stage of the season.

Having seen his under-strength and under-motivated side hammered by a rampant Manchester Utd at the weekend in the FA Cup, Wenger made the predicted changes, with Mathieu Flamini, Bacary Sagna, Gael Clichy & Emmanuel Adebayor all restored to the starting line-up. Whilst Milan, having seen Ronaldo ruled out indefinitely with a serious knee injury, opted to start 18 year old Brazilian prodigy Alexandrè Pato on his own up front, with former Leicester City keeper Zeljko Kalac recovering sufficiently from a dislocated finger to take his place between the sticks.

Wenger raised doubts about the quality of the San Siro pitch for the second leg in his post-match interview, but there were no such worries here as both sides found the surface perfect for their slick passing games. It was Milan who threatened first, Pato nicking the ball away from Cesc Fabregas to strike a volley that Tourè blocked, but at a cost. From the resultant corner, with Tourè off the pitch and Senderos not yet ready to replace him, Paolo Maldini forced a save from Jens Lehmann with a near post header.

But in truth that was as close as Milan came to the German’s goal for the remainder of the half, as Arsenal slowly but surely began to boss proceedings. Fabregas, seemingly recovered from his Old Trafford nightmare, picked out a superbly weighted clipped pass for the run of Adebayor, but the Togolese striker rushed his angled shot on the run and it flew into the stand. Soon after, Emmanuel Ebouè managed to do what many a wide player has tried and failed over the years, he bamboozled Maldini down the right, before cutting the ball back to Flamini, who struck his first time shot sweetly, but straight at Kalac.

Fabregas & Flamini each enjoyed a composed forty five minutes, and it was a fascinating tussle between the youthful pairing and the wily Milan trio of Massimo Ambrosini, Gennaro Gattuso & Andrea Pirlo, who gave as good as they got defensively, without ever looking like threatening at the other end. Fabregas did manage to find some space as the half drew to a close, bursting beyond Pirlo & Ambrosini to get into the box, but Adebayor’s square pass was poorly weighted and Maldini was able to hack clear to ensure a goalless first half.

With Nesta lasting just four minutes of the second half before being forced off, Arsenal began to sense an opportunity. Indeed, whilst the Italians waited to send on Marek Jankulovski as his replacement, they almost fell behind, Fabregas’ corner touched on at the near post and thumping off the oblivious Kaka’s chest, flashing inches wide.

The tempo (and noise-levels) raised, Arsenal began to dominate, Adebayor denied an opener by the linesman’s flag, and Ebouè dragging a glorious chance wide from 15 yards after a surging run down the right from Aliaksandr Hleb had created a shooting chance. Adebayor was then denied bravely by Kalac after he had gathered a Fabregas clip, and saw the Australian comfortably gather his low 20 yard volley, along with a stinging Fabregas strike, before Eduardo Da Silva, quiet for the majority of his 74 minutes, drew another save with a stretching left foot effort from the edge of the box (although the ball appeared to be flying over the bar anyway, and the referee gave a goal kick in any case).

It proved to be his last action as he was replaced by Nicklas Bendtner, whilst Pato was forced off with cramp a couple of minutes later, to be replaced by Alberto Gilardino. The Italians were content to sit back and protect their clean sheet for much of the match, but when they did venture forward, Kaka’s pass picked out Massimo Oddo in the box, but the right back showed exactly why he is a right back with a wild effort that went high and wide. At the other end there was still plenty of endeavour from Arsenal- Ebouè, like Adebayor in the first half over-hit a simple square pass for Hleb, with Bendtner slashing the pull back from the Belarusian way over the top, whilst Kalac did well to hold another powerful 20 yarder from Fabregas.

There might have been a real sting in the tale in the dying minutes as the intelligent Gilardino managed to get free at the near post for a Kaka corner, but his glancing header was well gathered by Lehmann, before the best chance of the night at the other end arrived in stoppage time. Theo Walcott, on for the increasingly erratic Ebouè, was the architect, working space for the cross on the right and standing up a superb cross that cut Kalac out of the equation and needed only the simplest of headers from an unmarked Adebayor at the far post. But, indicative of Arsenal’s evening, their top scorer somehow contrived to smash his header against the crossbar, and moments later came the final whistle, and the realisation of the importance of this missed chance.

It isn’t an impossible task facing Wenger’s young side (average age last night- 25) in the San Siro in two weeks’ time, and the likes of Fabregas, Hleb, Flamini & Clichy certainly showed they can live with Milan’s European footballing aristocrats of Pirlo, Gattuso, Ambrosini & Clarence Seedorf, Adebayor may have had a frustrating night in front of goal, but Kaladze, Nesta and then Maldini will not have had many more demanding evenings this season, whilst the Italians’ star man Kaka, and his teenage protégé Pato, were kept pretty well shackled throughout, even minus Tourè. But by the same token, the Gunners will have to take at least one of their chances in the second leg (if they are to proceed without the aid of penalties that is), and Milan’s defence will be an even tougher nut to crack in front of their home fans, whilst they will surely play at a higher tempo going forward than they did here.

One thing’s certain, it should be an intriguing second leg.