Success in this tournament is, therefore, the Gunners' only hope of qualifying for next season's Champions League.
Having lost five of their last six matches, it is little surprise that Arsenal are chalked up as a 12/5 (3.40) chance with dabblebet to seize the initiative in the tie by winning the first leg.
Milan are unbeaten in 13 matches in all competitions and Gennaro Gattuso's men are available at 11/10 (2.10) to heap yet more misery upon Wenger and his side with victory here.
dabblebet go 23/10 (3.30) that the first leg ends all square.
The Gunners have fielded a number of fringe players in this competition, but given the magnitude of this match for the visitors, Wenger will surely name a strong side in Milan.
Pierre-Emerick Aubameyang is ineligible for this tie and Alexandre Lacazette remains sidelined. Mesut Ozil and Henrikh Mkhitaryan could feature, along with Danny Welbeck.
For Milan, Luca Antonelli, Ignazio Abate and Andrea Conti are all out.
Milan to frustrate Arsenal?
Gattuso's side have kept a clean sheet in seven of their last eight matches and Milan are available at 7/4 (2.75) with dabblebet to keep Arsenal at bay.
Both teams to score
Despite their dismal form, however, Arsenal have scored in seven of their last nine away matches and dabblebet go just 2/5 (1.40) that the team from north London score here.
dabblebet also go 7/10 (1.70) that there are goals at both ends, a selection that would have landed in seven of Arsenal's last 11 matches.
Preview and predictions
Arsenal have been abysmal in recent weeks, but there is plenty of potential for the Gunners to play their part in an open and entertaining Europa League clash.
It is dabblebet's 10/11 (1.91) quote for at least three goals to be scored, therefore, could represent best value for punters ahead of Thursday's tie.