AC Milan did the Italian job tonight, breaking their English hex and condemning Arsenal to an almost certain exit from Champions League. Every weakness of the Gunners was exposed by a rampant Milan attack, resulting in a 4-0 thrashing that could have been far worse.

In the other evening's fixture, Zenit eked out a 3-2 win over Benfica in a blisteringly cold Russian night. Despite the weather, the game saw two genuinely sublime goals - as well as three comically bad defensive gaffes.

Both second-leg matches will be played on March 6 and the Champions League round-of-16 continues next Tuesday.

Arsenal endured one of their worst European nights, as a Milan side led by Robinho and Zlatan Ibrahimovic, ripped through their defense at will. The score line was Arsenal's heaviest loss in 222 European matches outside of qualification and leaves the Gunners staring at yet another season without silverware. They simply never got into the match and looked a shadow of the side that had triumphed so memorably at the San Siro back in 2008.

Robinho -- a player who has dropped a step or two -- was nonetheless too quick and crafty for an Arsenal midfield that looked stuck in toffee. Aaron Ramsey and Mikel Arteta looked lost against Milan's diamond formation, making basic errors and capitulating possession. Ibrahimovic, also not known for his turn of pace, repeatedly blew by Bacary Sagna and Thomas Vermaelen, putting the Gunners under withering pressure from the onset.

When Kevin Prince-Boateng scored the opener after only 15 minutes, it was deserved, as well as preventable. Keeper Wojciech Szczesny had cleared the ball right to Antonio Nocerino, allowing the Ghanaian to ghost in, chest the ball down and fire a superb fine strike.

The second goal was just as shameful, with Szczesny again gifting Milan an outlet that Ibrahimovic gleefully ran past Sagna to feed an unmarked Robinho. Laurent Koscielny, who was simply awful, stood and watched the header home. Things went downhill from there.

Vermaelen, who managed to make Koscielny look good tonight, fell down to allow Robinho to score his second score. Mercifully, Ibrahimovic capped off the affair by scoring from the spot after Johan Djourou tackled him rugby-style in the box.

And yes, it could have been worse. Arsenal were outworked, outthought, outclassed, outplayed and left undressed by a Milan team that was better in every area of the game. The attack-minded Gunners didn't have a shot on goal until well after the hour mark. Tactically, they were naïve, allowing a compressed Milan side to cut through them while declining to take the game out wide. The best you can say about their players tonight was some looked less cowed than others.

Arsenal are now left with serious questions, the same ones that have dogged this team for the past three seasons into their pronounced decline. Arsenal lack the playmakers and defenders needed to compete at the highest level.

These issues are apparent to anyone who has watched Arsenal struggle in the Premier League this season. In fact, they now face a grim fight just to reach the play-off slot for next year's European season. The only title realistically left in their reach is the FA Cup, and that seems a touch too far. Arsenal must recover from this debacle ahead of a decisive FA Cup game on Saturday against Sunderland.

Yet, Arsenal doesn't seem to have the desire to address these questions head-on. They remain unwilling to spend money to retain their top talent, and instead have placed their hopes on youngsters instead of relying on proven players. The verdict in Milan was plain. Tonight, it was boys against men.

The last remaining hope for English pride in this tournament would seem to be Chelsea, who face a tricky tie against Napoli next week. An English side has always reached the quarterfinals of the expanded tournament. Should Chelsea crash out, it would represent a new low for the Premier League game.

It was something of a wonder in today's other game in St. Petersburg. The arctic atmosphere and badly chopped-up field conspired to make long stretches of the game forgettable. What action we had however, will make highlight reels for years to come.

Zenit's Sergei Semak scored one of the goals of the tournament when he backheeled the ball into Artur's net. More remarkably, the play was started off by another backheel, with Alexander Kerzhakov flicking the ball from the endline to Vladimir Bystrov, who in turn flicked it into Semak's path. It was a one-in-a-hundred goal that nicked off the post and past the bewildered Benfica keeper.

That strike topped Zenit's first goal; a delicious sidefoot volley from Roman Shirokov off a cross from Tomas Hubocan that cleanly beat Artur. And, it certainly exceeded their winner, which was a gift from Maxi Pereira, who played the ball right into Shirokov's path with only a minute left.

But though Zenit's goals had a touch of genius about them, their goalkeeping was more Chaplinesque.

Spelling the injured Vyacheslav Malafeev, Yuri Zhevnov turned in one of the worst performances in a net I've ever seen from a professional. First, the `keeper failed to collect a tamely hit free-kick by Oscar Cardozo, instead setting up Maxi Pereira. The bewildered defender couldn't miss from four yards. Then, with three minutes left to play, Zhevnov did it again, limply patting a scuffed shot from Nicolas Gaitan right to Cardozo for a score that was more low comedy than art.

It was perhaps fitting to the run of play that Benfica switched off to concede the winner only 90 seconds later, but they have the advantage. Zenit? They got a win, but need to find a `keeper, stat.