It’s a case of fallen giants at the San Siro on Thursday.
Arsenal are currently in disarray with the pressure mounting on manager Arsene Wenger.
The Gunners can salvage their season in the Europa League, but face a stern test against the resurgent Rossoneri in this intriguing last-16 first-leg clash.
Just like Arsenal, AC Milan languish well off the domestic title race, sitting in seventh place in Serie A following a disastrous start to the campaign.
However, gritty club hero Gennaro Gatuso has steadily built momentum since taking over the helm in November, with the club also reaching the Coppa Italia final.
Milan spent £200m on signings in the summer and Gatuso has galvanised those acquisitions with promising younger players to remain unbeaten in 12 matches in all competitions.
So who should Arsenal be wary of in Italy?
During the San Siro summer spending spree, Milan scooped this Italian general for £38m and considering his credentials, that was a bargain.
He helped guide Juventus to six successive Serie A titles and has established himself as one of the world’s finest defenders.
The 30-year-old has gelled with his team-mates as Milan have built a tight backline, which has managed to go without conceding in 10 hours of play.
With Arsenal's record signing Pierre-Emerick Aubameyang and fellow striker Alexandre Lacazette unavailable, it will be an almighty task for the likes of Danny Welbeck and Henrikh Mkhitaryan to unlock this stubborn rearguard.
Liverpool fans might recognise this name.
The Spaniard struggled to settle during a five-year stint at Anfield and left for Milan in 2015.
However, Suso has flourished in Serie A with energetic and piercing play from the flanks.
He’s been so impressive in recent months that the 24-year-old has increasingly been linked with a move back to the Reds to replace the hole left by Philippe Coutinho.
Arsenal’s fragile defence will not welcome the sight of Suso.
This 20-year-old striker, in just his second campaign in the first team, is turning heads in Milan.
Twelve goals in 29 appearances have proven the Italian’s potential and he has been described as a “true No.9” in the national press.
Again, the beleaguered Gunners backline will be concerned by Cutrone’s physical strength and imposing aerial ability.
Another one for Liverpool fans, along with supporters of Chelsea and Swansea.
Borini had a turbulent Premier League spell and returned to his homeland on loan from Sunderland in June.
His first 25 appearances were fruitless, but Borini scored in three consecutive matches in February to reignite his stint in Italy.
Perhaps his confidence has been boosted under Gattuso and he could be a threat from off the bench.