Celtic kick off their impossible quest of qualifying for the knockout rounds of the UEFA Champions League for the second consecutive year with a trip to northern Italy to face one of the world's most famous football clubs in one of the world's most famous stadiums. Milan have fallen away from the heights they've hit in the last 10 years, reaching 3 Champions League finals, winning one in 2007, but are still more than a match for the Scottish champions.
Celtic hit the ground running following the international break, comfortably seeing of Hearts' kids 3-1 at Tynecastle, whereas Milan left it late to salvage a point against Torino, with an equalising penalty from the mercurial Mario Balotelli coming in the 96th minute. Both will be nervous coming into this tie for very different reasons.
Milan's start to the season hasn't been brilliant, defeat to Verona, easing past Cagliari at home before their unconvincing weekend slip up to Torino . Their performances in all three give Celtic the confidence required to take something from Milan.
And the Rossoneri's injury troubles are at their worst. Without a fit, recognised full back, Milan will also be void of the creativity of Stephan El Sharaawy, Riccardo Montolivo and returning hero Kaka. In total Milan will be without 8 first team players, but Montolivo is perhaps the most notable.
The Italian is a pass master, the man tipped to take over from Pirlo for the Azzuri will be out of action on Wednesday night. The midfield runs from deep of Muntari and Poli will be significantly less effective without the vision of the former Fiorentina man.
And the loss of full backs Ignazio Abate and Mattia De Sciglio is exactly what Neil Lennon's Celtic must exploit. Every single goal scored by Celtic away from home in Europe last season came from a wide area, as did the two goals lost to Verona in Milan's Serie A curtain raiser.
It would be a massive risk to play with Boerrigter, Samaras and Kris Commons, but Celtic have nothing to lose, and should throw the kitchen sink at a Milan side on their knees.
As much as Celtic have potential to hurt Milan, Milan's potential to hurt Celtic is far greater. The loss of El Sharaawy is a blow, but Milan can rely on the fire power of young winger M'Baye Niang, the enigmatic Mario Balotelli and Alessandro Matri - the latter has already helped himself to a goal against Celtic in last season's Champions League with Juventus.
Milan press high without the ball, and will most probably control the ball for the majority of the game. The Celtic back four must be constantly vigilant, and their midfield must be warned of the deep runs of Milan's midfielders, as its one of the most useful weapons in European football.
For Celtic, the line up will be a bit if a mystery. Anthony Stokes (currently in the form of his life) is seldom picked for Champions League games, but with only Pukki available, his lack of time with the first team squad since his arrival from Schalke making him a doubt to start, it may well be Stokes' time to shine on the European stage. The choice of Mulgrew or Boerrigter will spell out whether Celtic will play it safe, or go for the jugular.
For Milan, it may be a case of plugging the leaks. With so many injuries, there is a frailty of the team that Massimilliano Allegri will do well to cover up. The devastating counter attacking football Celtic are renowned for in Europe may raise a few eyebrows, and set up a tasty fight for second place in the "group of champions".
Don't get me wrong, I'm not saying for one minute that Milan's crisis renders them in the same league as St Mirren or Kilmarnock. I fully expect whatever 11 players turn out for Milan to be capable of seeing off Celtic. But if there was ever a time you wanted to play Milan in the San Siro - it's now. If Neil Lennon gets his tactics right, (and that's a big if) Celtic have the capability themselves to overwhelm a makeshift Rossoneri on the break. I'm not saying it's expected or a certainty, but just watch this space.
Milan-Celtic is available to watch on Sky Sports 2 from 7:30pm