Two European heavyweights lock horns in pre-season on Wednesday with Arsenal taking on AC Milan at the Singapore National Stadium. It promises to be an exciting battle between two highly regarded tacticians, Mikel Arteta and Massimiliano Allegri, and it should offer a glimpse into both teams' pre-season preparations.Arsenal have borne the cross of settling for silver medals instead of silverware like a curse. The Gunners constantly seem to be getting closer to the Premier League mountaintop each and every season before shooting themselves in the foot and handing the competition a free pass in the final straight.With Manchester City nowhere near their best last season, it appeared as though the stage was set for Arsenal's coronation. However, the Gunners ended up tucking their tails between their legs watching the breakneck speed at which Liverpool, under new manager Arne Slot, raced to the title.They have added Christian Norgaard, Martin Zubimendi, Noni Madueke and Kepa Arrizabalaga to their roster this summer. The North London outft also kicked off their pre-season during the weekend against Watford, winning 2-0 thanks to goals from Ben White and Kai Havertz.Meanwhile, their Wednesday opponents AC Milan have brought Max Allegri back into the fold. The Italian coach was sacked by Juventus over behavioural concerns after a meltdown of sorts during and after the Bianconeri's 1-0 win over Atalanta in the 2024 Coppa Italia final. Allegri reportedly got aggressive with the referee and threatened a journalist during the post-match celebrations. He has taken the reins at San Siro and replaced Sergio Conceicao, whose one-year stint at AC Milan was lacklustre to say the least.Arsenal vs AC Milan Head-to-Head and Key NumbersIn eight meetings between the two sides, Arsenal have been victorious four times while AC Milan have won two times. Two matches have ended in a draw.Arsenal have won the last three meetings between the two sides.The Rossoneri have conceded eight goals and scored just one in their last three matches against Arsenal in all competitions.AC Milan failed to qualify for European football last season.Arsenal vs AC Milan PredictionAC Milan have parted ways with two of their key players, Tijjani Reijnders and Theo Hernandez and are also navigating life under the watch of a new coach. Both managers will experiment with their squad but Arsenal are likely to emerge as the winners here.Prediction: Arsenal 2-1 AC MilanArsenal vs AC Milan Betting TipsTip 1: Result - Arsenal to winTip 2: Game to have over 2.5 goals - YesTip 3: Both teams to score - Yes