Pioli’s debut to his Milan reign did not follow the script as Marco Calderoni caused some heartbreak in the 92nd minute and the Rossoneri were forced to share the spoils with Leece in a 2-2 draw on Sunday. Despite the result, Pioli was upbeat about positives and will be eager to build on them in the coming weeks. It might just be 90 minutes into Pioli’s reign but the coming fixtures are indeed pivotal ones that could well determine whether or not the 54-year-old  potentially ends up like his predecessor Marco Giampaolo.

It would be unfair on Pioli to out-rightly say his future at the club could be dependent on a couple of games considering he has barely made any impact at all. But anyone would know that a bad run of games puts him in even worse conditions than Marco Giampaolo once saw himself, considering he was brought in to be the “saviour” from a bad situation.

Two years is still a lot of time (at least that’s what Pioli’s contract with Milan says) but what happens between now and the end of the season will determine if the Italian stands a future with the Rossoneri. And on shorter term, what happens between now and December will determine if he’ll even last till the end of the season in the first place.

As history will suggest, the most important phase of a new manager’s reign is usually the beginning and that’s where the ideologies, tactical discipline and personnel management must be implemented from the onset. A new manager’s dream is to ideally get a favourable run of fixtures as well. Unfortunately, that’s not the case for Pioli and his Milan side.

With that in mind, let’s take a look at the crucial run of fixtures that could literally determine Pioli’s future with Milan (if he is destined to have one with the club).

Roma vs Milan (27th October)

In just about four days from now, Milan take on sixth place Roma at the Stadio Olimpico. The Giallorossi have not been in their best form as well as they are without a win in their last three games in all competitions, drawing all three of them (Skysports). Milan can take further solace in the fact that they have a good record against Roma and the last time they lost to the Giallorossi dates far back as 2017.

Despite all of that, Roma’s only loss in the Serie A this season was a 1-0 loss to Atalanta and in plain terms, Roma have not been at their “best” but they barely lose as well and to settle for a draw seems to be their worst-case scenario. This fixture looks all set out for yet another draw between both sides and we all know what two consecutive draws could mean to Pioli early on in his Milan managerial career.

Milan vs Spal (31st October)

This is the fixture Milan can use to fire back on all cylinders. Spal have struggled this season and currently lie in the relegation zone at 18th place in the Serie A standings. A win should be expected for Pioli – on paper at least. This game could be crucial in the sense that Milan would go into the game as heavy favourites and anything short of a convincing win will spell serious danger for Pioli and his future at the club.

Milan vs Lazio (3rd November)

Lazio sit only one position behind Roma and are currently in seventh place on the standings. Their two losses so far have come from Inter and a shock defeat to Spal (surprisingly). Despite being in seventh place, Lazio are only two points ahead of Milan so it’s a tough call to determine who would be better going into the game. All things going well though, Milan should have stabilized at this point and if the likes of Calhanoglu and Piatek keep decent performances up until this period, the game could well be in Milan’s favour and they could yet scrap out a win.

Now this game once again is similarly crucial as it precedes what will be Pioli’s biggest test in his Milan career early on as his side take on Juventus next after this fixture. Even with players in top gear, playing Juventus at the Allianz Stadium is an herculean task for anyone talk less of a team going there low on confidence. Hence, the Lazio game is a must-win for Pioli at all costs.

Juventus vs Milan (10th November)

Juventus (as always) have set the standard once again as the team to beat in the Serie A. Sarri’s men may not have been at their “dominating” best so far they’ve done the all-important job of getting results and remain the only unbeaten side in the Serie A this season. Juventus have already won against the likes of Napoli as well as the new and upgraded looking Inter this season and based on what we’ve seen so far, this fixture should be an easy win for the Bianconeri.

This fixture hasn’t been kind to Milan as well, regardless of the venue as Juventus have won all eight of the last meetings between both sides (fctables) and it’s looking like a ninth consecutive win when they meet in less than a month. This shouldn’t trouble Pioli much as he would be forgiven for losing to the champions anyway.

But on the flip side, a shock win for Pioli could have a massive effect on the Milan side in terms of confidence and it could be the turnaround moment to revive their already faltering season. It would also bring some sense of calm between Pioli and the Milan hierarchy and it could secure his future at the club – at least for the nearest reality.

Milan vs Napoli (23rd November)

There’ll be yet another international break in November between the 11th and 19th (EURO 2020 qualifiers) and club action resumes back the following weekend. Just when you think Milan would be aiming to get back to winning ways after a difficult clash in Juventus, the reward is yet another heavyweight clash with Napoli. Carlo Ancelotti’s men currently lie fourth in the Serie A standings and their two losses so far have come from the hands of  Juventus (not surprising) and an upset from Cagliari who have been impressive so far and lie in fifth place, only two points behind Napoli.

It could be a tough clash and of course, the previous result from the Juventus game will have a big influence on Milan’s character going into this game. It is yet another crucial clash as Juventus should most likely (speculation) win the previous game and this game would be the game to bounce back. However, Napoli are no ride over as well and it could even be two losses on the bounce if proper caution isn’t taken. The fact that there was an international break in between will only make the tension build further and make the wait longer for a return to positive results.

It’s premature to say anything about Pioli’s future right now but these crucial games could yet tell us or give a hint of where his chances lie with the club moving forward. If Pioli is to have a better story than Giampaolo did, the action starts now and he must try to take as many points as possible from these next run of games. None of them would come easy but I’m sure Pioli was well aware of the volatile state of the Milan hot-seat before he accepted the job. To that effect, we can only hope the Italian has some master-class lying in wait ahead of these fixtures.