AC Milan vs. Arsenal: 3rd Time's a Charm for the Gunners at the San Siro?

Feb. 15, 2012 will be have a certain amount of deja vu coursing through it for a handful of Arsenal players.

Then again, it might just be Bacary Sagna, Robin van Persie and Arsene Wenger who are the most affected (more on that later.)

When the Gunners hop off their chartered bus at the docking area in the San Siro's periphery on Wednesday night, they'll be doing more than heading to a locker room.

They might be headed for an incredible feat.

Wednesday's Champions League Round of 16 first leg marks the third time Arsenal have played at the San Siro in Europe's premier club competition since 2003.

In November of '03, they'd been tasked with finding a way to win against Inter Milan in order to preserve their ambition of progressing past the group stages. Three points were essential for Arsenal at that juncture, who were in danger of seeing their continental campaign end prematurely.

Enter Thierry Henry.

Despite dealing with a hamstring problem, the French forward was at his uncompromising best, scoring a vital hat trick by way of that inimitable languid approach toward goal as Arsenal shrugged off a sluggish first half performance (it was 1-1 at the break) and went on to throttle the Nerazzuri 5-1, all but guaranteeing their inclusion in the knockout stages.

It was a sweet measure of revenge after having been swept off the Highbury pitch 3-0 just two months before by that same Inter side.

Fait accompli, fast forward four-and-a-half years later to another memorable Arsenal exploit.

Facing AC Milan in the return leg of the 2008 Champions League Round of 16, the Gunners were raring for a victory after ending the first leg in a 0-0 draw at the Emirates.

Enter another, then-rapidly blossoming Arsenal legend.

No, not Van Persie (he was an unused substitute that night, while Sagna was the starter at right-back).

Cesc Fabregas, who scored 13 goals in all competitions for the club that season, enjoyed one of the finer strikes of his career that unforgettable night. That night Arsenal swept aside Hleb-gate as well as a rapidly-aging Milan side in an engrossing 2-0 victory that saw them earn a quarterfinal draw with Liverpool.

So onto 2012. Another four-year leap. Can lightning strike thrice in Milan?

The San Siro is no cakewalk, and AC Milan always seem to have bags of experience within the side—which makes it all the more remarkable that Arsenal have enjoyed such success.

They'll be facing a stronger AC Milan side this time around—one brimming with confidence/arrogance?—who are currently first in Serie A on 47 points, although second-place Juventus sit just two points back with two games in hand.

The Rossoneri's form of late hasn't exactly been spellbinding—they've managed just 13 points from their last seven games (all competitions)—a run which has seen him lose lose to Inter, Lazio and Juventus.

That plays into the hands of Arsenal, who after enduring their own stagnant form during January (three consecutive EPL losses), have come roaring back with a pair of league victories in February, during which they've outscored their opponents 9-2. Obviously the 7-1 win over Blackburn helps that reasoning along, but still.

There are an abundance of plot lines shaping up ahead of kickoff tomorrow—and rest assured, the pregame punditry will dig a few more out from the proverbial rubble to add some extra spice to the proceedings. Aside from Arsenal's recent success at the San Siro, here are a few other developments to keep track of:

• Arsenal face Zlatan Ibrahimovic, now a Milan striker, for the first time since the 2010 Champions League quarterfinals, when the tall Swede scored two first-half goals for Barcelona in the first leg at the Emirates in an eventual 2-2 draw.
• Mathieu Flamini, former Arsenal midfielder and part of the side that won at the San Siro in 2008, now plies his trade with Milan. The Frenchman will be out due to injury (he's still recovering from offseason knee surgery).
• Thierry Henry makes his first visit to the San Siro since that unforgettable night, now eight years gone. (He moved to FC Barcelona before the '07-08 season.)

The man with 229 goals to his name while wearing the red-and-white shirt has been a godsend since rejoining the club for a six-week loan spell back in January.

If this does indeed mark his final farewell tour as an Arsenal player—then what a sending off it's been.

There's the winner scored against Leeds back on Jan. 9, the penultimate goal against Blackburn two weeks ago and the predatory finish against Sunderland last Saturday to deliver the Gunners to a 2-1 victory at the Stadium of Light.

I've always been prone to fits of poetic fancy, so bear with me here. Henry's latest turn with the club that made him a star has all the markings of the all-knowing guide of the iconic "hero's journey."

Henry has assumed the role of mentor for Arsenal in recent weeks, providing a young side with a reassuring presence.

He has rescued them from the jaws of defeat on numerous occasions, and while those goals have stirred my blood, my favorite moments—the ones I'll remember vividly—have been when the camera has caught him in animated discussion with one of the younger Arsenal players while sitting on the bench.

At 34, he knows his best days as a player are behind him, and he has accepted his current role with the grace one would expect of such a deity. He is there not to be the star. He is there to instruct and help where he is needed. There's a wonderful humility to that.

After Wednesday's match, he'll be leaving London Colney for New York, where he will rejoin MLS side New York Red Bulls. Arsenal will be left to forge on without their guide.

But I think they're ready to go on ahead. In the afore-linked ESPN Soccernet article, Henry mentioned how he wants to leave Arsenal with a "parting gift"—a victory against the Rossoneri.

Given his history of profligacy in the arena where tomorrow's match takes hold, and the mythic quality his return has taken on (a goal in the final stages of his final home match for Arsenal, a goal at the death of his last-ever EPL match), would it be too far removed from the realm of possibility to expect a glorious and symmetric third and final act to his last go-round with Arsenal?

Stranger things have happened. And hey, you know what they say about the third time.

I'm ready to be charmed.