Weblog: The football punter
Gunners losing run could be extended by Milan
Arsene Wenger has come through a lot of tough times in his 21 years and five months at Arsenal but the Gunners' four-match losing sequence has equalled the worst he has suffered during his time in charge and another defeat looks on the cards at the San Siro.
It is getting difficult to see how Wenger can see out his two-year contract with the Europa League offering the only realistic hope of salvation.
He signed his latest contract extension in the afterglow of last season's FA Cup final victory over Chelsea but supporter discontent has never really gone away and the 'Wenger out' banners and chants returned during Arsenal's dismal 2-1 loss at Brighton on Sunday.
The result ended any hope of challenging for a top-four finish and leaves Arsenal totally reliant on the Europa League in their quest to deliver Champions League football.
They are odds-on favourites to come through their tie with Milan and odds-on to avoid defeat in the opening leg, although neither of those prices reflect the scale of Arsenal's fall from grace and the quality of Milan, who are on the rise and unbeaten in 13.
Milan have had a lean spell in recent seasons and haven't played in the Champions League since the 2013-14 campaign.
Despite the improvement under Gattuso, they are seventh - nine points adrift of the top three - and, like Arsenal, will be looking at the Europa League as their best hope of Champions League qualification.
But the mood of the club has lifted and the fans have a Coppa Italia cup final against Juventus to look forward to in May.
Whether or not Gattuso is the long-term answer to their problems remains to be seen but he knows the club inside out, having spent 12 seasons there as a player, and has shown a willingness to hand opportunities to some of the club's younger players.
Two of Milan's youth products - right back Davide Calabria and striker Patrick Cutrone - have become regulars and Cutrone is the club's joint-top league goalscorer with six.
The team's biggest weakness is up front with nobody seemingly capable of scoring on a prolific basis. But they look strong at the back with 75-cap Italy international Leonardo Bonucci anchoring the defence.
And a couple of committed, organised performances may be all it takes to overcome an Arsenal side in such disarray.
Arsenal's first-half performance at Brighton was abysmal - even by their recent standards.
They had Pierre-Emerick Aubameyang's goal-poaching instincts to thank for reaching half-time with just a single-goal deficit but the Gabon striker is ineligible to play against Milan and Arsenal cannot call on injured forward Alexandre Lacazette.
That equates to more than £110m worth of attacking talent they cannot use and it will make it tough for them to open up a Milan side who have kept six successive clean sheets
Milan may lack the offensive quality to put the tie to bed but they are the likelier first-leg winners and look value at odds-against.