Both fallen giants in their respective leagues, Arsenal and AC Milan clash in a mouthwatering friendly battle at the Kallang Stadium in Singapore on Wednesday.

Mikel Arteta's men headed to the Far East on the back of a 2-0 behind-closed-doors triumph over Watford, the first step towards ending a torturous run of three straight second-placed finishes in the Premier League.

Meanwhile, Milan are taking to the field for the first time since Massimiliano Allegri returned to the club, as the Italian succeeded Sergio Conceicao following the latter's failure to take the Rossoneri into Europe.

Here, Sports Mole takes an in-depth look at the head-to-head record and previous meetings between the two sides.

Head-to-head record

Previous meetings: 8

Arsenal wins: 4

Draws: 2

AC Milan wins: 2

Excluding a December 2022 friendly during the last World Cup - which Arsenal won 2-1 - there have been eight competitive meetings between the Gunners and AC Milan over the years.

The North London giants have emerged triumphant in four of those contests, including each of their last three across the Europa League and Champions League, although one of those successes was for nought.

Indeed, the 2011-12 Champions League saw Milan and Arsenal collide in the last 16, and Arsene Wenger's men nearly pulled off the improbable after a crushing 4-0 first-leg loss at San Siro.

The Gunners raced into a 3-0 lead at the Emirates Stadium a couple of weeks later, but there was to be no almighty comeback in the English capital as Milan progressed to the quarter-finals.

However, Arsenal dumped their Italian counterparts out of Europe in both 2008 and 2018; the former year saw them become the first English team to ever defeat Milan at San Siro, as Cesc Fabregas and Emmanuel Adebayor struck in a 2-0 last-16 second-leg win.

A decade later, Wenger masterminded a 5-1 aggregate triumph over the Rossoneri during the 2017-18 Europa League last 16, as the Gunners again prevailed 2-0 away before completing the job with a 3-1 home victory.

The two titans also met with silverware on the line three decades ago when they contested the 1994 UEFA Super Cup, firstly playing out a goalless draw at Highbury.

Seven days later, Milan made the most of home advantage, winning 2-0 to clinch the continental title as Zvonimir Boban and Daniele Massaro breached David Seaman's net.

Previous meetings

Mar 15, 2018: Arsenal 3-1 AC Milan (Europa League)

Mar 08, 2018: AC Milan 0-2 Arsenal (Europa League)

Mar 06, 2012: Arsenal 3-0 AC Milan (Champions League)

Feb 15, 2012: AC Milan 4-0 Arsenal (Champions League)

Mar 04, 2008: AC Milan 0-2 Arsenal (Champions League)

Feb 20, 2008: Arsenal 0-0 AC Milan (Champions League)

Feb 08, 1995: AC Milan 2-0 Arsenal (UEFA Super Cup)

Feb 01, 1995: Arsenal 0-0 AC Milan (UEFA Super Cup)

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Written by
Ben Knapton