On 9 February, Milan took a shock 2-0 lead into the half-time break over bitter rivals Inter, but ultimately came up short, shipping four second half goals and collapsing in gut-wrenching fashion.
On Tuesday evening, the very same team found themselves staring down the barrel of a two-goal deficit to Juventus. This time however, they showed enormous spirit and quality to rumble the champions of Italy, claiming a precious 4-2 victory.
It was a telling demonstration of just how far this group of players, previously branded as sub-par and unworthy of the Rossoneri shirt, had come. Speaking after this incredible comeback, talisman Zlatan Ibrahimovic cursed the fact he'd arrived midway through the season, claiming things could have been very different had he taken to the field from the off.
This, of course, is vintage Ibrahimovic - making a claim which can not ever be disproved, and only adds to the aura and mystique that surrounds the big Swede. But although it's similarly on-brand to his usual nonsense about lions and Chuck Norris comparisons, there may be more behind this particular sound bite.
With Tuesday evening's win, Milan have now reached the dizzying heights of fifth place, having languished in mid-table for the majority of the year. Mathematically however, they remain 26 points behind defeated leaders Juve. That's more than half of I Rossoneri's current points tally.
So, to throw the Italian giants into the hypothetical hat for any title race may feel rather premature. But this is undoubtedly the longest green shoots that their tortured fanbase has seen in almost a decade.
Admittedly, all the attention and praise falls onto the broad and welcoming shoulders of Zlatan, but an unlikely hero has emerged at San Siro over recent months. Wanted by no one, and seemingly raising the poisoned chalice to his lips, Stefano Pioli has come out the other side alive, and with plenty of stock to his name.
Having replaced Marco Giampaolo in October, who himself only lasted seven games, there was little hope that Pioli would be the catalyst behind a Milan revival. But with the exact same group of players as his predecessor (plus Ibrahimovic), the ex-Fiorentina boss has turned around this sinking ship, while also breathing life into the faltering careers of many Rossoneri flops.
If you'd asked supporters which players they'd prefer to never darken the San Siro doors again, they'd have probably offered you a list the size of the stadium itself. Franck Kessie, Hakan Calhanoglu, Andrea Conti, Ante Rebic, and Rafael Leao are a handful of stars who did not cover themselves in glory.
But they have all been revelations since the turn of the year. Kessie is becoming the classy operator in the midfield that he had once promised to be at Atalanta, while Calhanoglu has finally begun to add some end product to his impressive industry.
Goals, which were once so hard to come by for this side, are now flowing freely, with Rebic notching 10 in 20 matches, while Leao has also found himself on the score sheet in recent weeks. And Conti is now part of a tight-knit, resolute defence, spearheaded by the arrival of warrior Simon Kjaer and captain Alessio Romagnoli.
So it's fair to say, there have been drastic improvements all over the pitch. This group of misfits and oddballs have all been given a purpose, and with a man who genuinely believes in them and plays to their strengths, they have found their true calling at San Siro.
And it's not like this squad has always been devoid of talent. Defender Theo Hernandez has been the undisputed star of the show, and his relentless, powerful displays have earned him the reputation as Serie A's best left-back.
I Rossoneri also possess one of the star holding midfielders in Italy too, in Ismael Bennacer. The combative Algerian was unfancied by Giampaolo at the start of the campaign - which ultimately proved to be a major factor in his downfall. But the 22-year-old has unleashed the talent we all knew he possessed under Pioli, and he provides a formidable presence at the base of the midfield.
And of course, there's Zlatan. The man whose winning mentality and high expectations caused the entire squad to take a much longer look in the mirror.
So, with such a strong core, a manager who has the players' trust, and an ability to perform at a level greater than the sum of their parts, are these the foundations of a title challenge?
Well, it's unlikely. Despite this new-found stability, a cloud of uncertainty still hangs over San Siro. Despite Pioli's heroics, he seems destined to be ousted from his seat at the end of the season, with football guru Ralf Rangnick set to take over the entire running of the club, including managerial duties.
It will be a harsh end for the current boss, but he can leave with his head held high. For Milan, the much-needed squad revolution now seems far less urgent. Pioli has proved over the past nine months that the rescue mission is far less drastic than previously anticipated.
Rangnick is a man who enjoys working the transfer market however, and he'll be keen to stamp his own signature on the squad, so changes may be made come what may. And there is always room for improvement.
In the end, the gap to the top of the table may be too vast to close in the space of 12 months for this new-look Milan side, with the likes of Atalanta, Inter and Juve continuing to strengthen their already stellar squads. Frankly, I Rossoneri may have their work cut out to maintain the current gap as it is.
But for once, there is positivity and hope in Milan. Hope that this core group of players could be the start of a new era. Hope that the return of the glory years is just around the corner. Hope of a scudetto.
And who are we to tell them not to dream?