It’s not every match day that winds up on a holiday, and although Halloween is a pretty American holiday, just because it’s a bigger deal on my side of the Atlantic doesn’t mean it can’t affect my favorite club in Italy. Sure, I don’t expect to see Nicolò Zaniolo walk into the Stadio Olimpico in a costume instead of a Tombolini suit, or for José Mourinho to walk the touchline dressed like a ghost. Nevertheless, following the Giallorossi is sometimes a spooky affair; other than a curse from ancient Roman spirits, how else could you possibly explain all of the injuries at Trigoria?

Roma vs. Milan: October 31st. 20:45 CET/3:45 EDT. Stadio Olimpico, Roma.

Even without Halloween looming, tomorrow’s match against A.C. Milan has the potential to be quite a frightening affair. Although there were a couple minutes against Cagliari where Romanisti may have worried about a loss, tomorrow’s match against Milan will certainly be a more stressful event throughout the entire match. Gone are the days of A.C. Milan, the sleeping giant; even with the loss of Gianluigi Donnarumma this summer (and the seemingly inevitable loss of Franck Kessié next summer), Stefano Pioli’s side have only been outshone by their cross-city rivals Inter in recent years with regards to a return to form.

Milan’s hot form aside, most outside observers peg this match in a similar manner as last weekend’s Derby del Sole: a massive match between two clubs vying for Champions League qualification, and perhaps even more. Both the Giallorossi and the Rossoneri are towards the back end of an incredibly tiring run of matches, so look for a hard-fought match where substitutions could play a key role.

What To Watch For

Who Strikes First: Rafael Leão or Tammy Abraham?

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Any time a José Mourinho side goes up against another big club, it’s safe to bet that defensive integrity will be a main feature of the match. Roma’s recent 0-0 draw against scorching-hot Napoli is a prime example; sure, it wasn’t the decisive win that many Romanisti would have loved against Luciano Spalletti’s men, but considering the Giallorossi were the first to get any points off of I Partenopei, it was a very important result. Similarly, if I was a betting man I’d expect a low-scoring draw to be the end result of this match, but that doesn’t mean that the attacking ability on display at the Olimpico tomorrow will be lacking. Both Milan’s Rafael Leão and our very own Tammy Abraham have proven to be the exact kind of forward you build around to start the season, with Leão contributing five goals and Abraham contributing four goals across all competitions.

We’ve already spilled a lot of digital ink on Abraham at Chiesa di Totti, so I’ll focus more on Leão here. The Portuguese striker might be less of a global superstar than his fellow Milan strikers Olivier Giroud and Zlatan Ibrahimović, but his ability as a striker (particularly for his age) shouldn’t be questioned. Where Abraham thrives on aerial duels and as a finisher, Leão is much more of a dribbler, and as such he could cause a lot of headaches for Gianluca Mancini and Roger Ibañez. The duo have handled Victor Osimhen and João Pedro handily in the past week, but Leão’s Serie A WhoScored rating of 7.24 doesn’t lie; aside from Sandro Tonali, he’s the most intriguing player Milan put out on the field on a weekly basis.

Can Roma Make Life Hell For Milan’s Backup Keeper?

Photo by Claudio Villa/AC Milan via Getty Images

The other side of the pitch from Rafael Leão is arguably where Milan is at its weakest. With Mike Maignan still out for another two months after getting surgery on his left wrist, Ciprian Tătărușanu (try typing that ten times fast) is the Rossoneri’s man between the sticks until further notice. No offense to Tătărușanu, but if I was José Mourinho, I’d be far less worried about facing the Romanian shot-stopper than his French team-mate; in fact, I would try to punish the 35-year-old backup from the word go in an attempt to break him down as quickly as possible.

In his three Serie A matches this season, Tătărușanu has been a passable replacement for Maignan, conceding four goals in three matches. Aside from a clean sheet against Torino on Tuesday, it’s largely been due to Milan’s attacking prowess that Il Diavolo have been able to keep the good times rolling without their Gianluigi Donnarumma replacement. If Roma’s attacking corps can finally find their shooting boots against Milan, it could mean that the Giallorossi keep the Stadio Olimpico’s status as a fortress for yet another week.

Does Felix Afena-Gyan Get A Second Look?

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There’s little chance that José Mourinho will change much of anything with his starting eleven heading into this match. The Special One has already admitted that there are very practically no alternatives on the bench that he’s comfortable with rotating in against the minnows, let alone big opponents like Milan, so at most I would expect to see someone like Eldor Shomurodov or Stephan El Shaarawy come in as a way to rest Henrikh Mkhitaryan, who’s been showing some seriously poor form in recent weeks.

The one exception to José’s hesitance to utilize his depth options may be Felix Afena-Gyan, who came on as a surprise substitution for Matias Viña in the midweek match. Afena-Gyan has been lighting up the Primavera side ever since he signed for Roma in January of this year, scoring six goals in five appearances so far this season. Those performances in tandem with his solid half-hour on the pitch for the senior side have apparently won Mourinho over enough to convince him that Afena-Gyan should be training and playing exclusively with the first team until the end of 2021. The fact that he’s ineligible for Conference League games strongly suggests that the Ghanian forward will see time in Serie A over the next two months. If he impresses when he plays, he might not even have to go out on loan to find playing time in the second half of the season, and Roma might be moving from strength to strength in an already-deep attacking corps.