The champions fumbled two points in stoppage time last week, before crashing out of the Coppa Italia on Wednesday; meanwhile, their hosts have picked up four points since the winter break to sit 11th in the Serie A standings.
Match preview
Occupying third place in the table ahead of the 18th match of their league campaign - marking its midway point - Milan's late collapse at home to Roma last Sunday allowed old foes Juventus to sneak in and steal second spot.
Both clubs trail seven points behind leaders Napoli, after the Rossoneri endured a dismal final five minutes against Jose Mourinho's men, during which they conceded twice to wipe out an advantage earned by earlier strikes from Pierre Kalulu and Tommaso Pobega.
Then, having played with a one-man advantage for almost an hour of their midweek defeat to Torino, they were stung deep into extra time and made their latest painful exit from the Coppa Italia: Milan have not lifted the trophy now for some 20 years.
Nonetheless, Stefano Pioli's side will meet current cup holders Inter in next week's Supercoppa Italiana, to be played in Saudi Arabia, and are also through to the Champions League's last 16, where they tackle Tottenham Hotspur next month.
First, though, they travel south to face Lecce on Saturday, when they will seek to make up ground lost to both Napoli and Juve, who clash at Stadio Maradona a day earlier.
Milan are unbeaten in their last eight league meetings with their Puglian counterparts - winning five times and scoring 20 goals in the process - so precedent is certainly on their side, if not current form.
In all, Lecce have won only two of their 32 top-flight fixtures against Milan - and none since 2006 - but recent events have led some to suggest they could push the Scudetto holders all the way this weekend.
Marco Baroni has steered the Giallorossi to a five-game unbeaten run either side of the World Cup break, and they could now go six-in-a-row in Serie A for the first time since 2012.
Remarkably, the last time Lecce kept clean sheets in successive Serie A matches came back in that year too, but conceding just four goals in their last six competitive games suggests that Baroni's men could now shut out their illustrious visitors.
A rain-soaked 0-0 draw at Spezia last week pulled them 10 points clear of the relegation zone halfway through their latest comeback campaign, and the Serie B champions are on course to extend their stay among Calcio's elite into next season.
Making the most of home advantage could prove crucial in that regard, and as Lecce have won their last two matches at Via del Mare, recording a third straight top-flight win there for the first time in 19 years is perhaps not out of the question.
Lecce Serie A form:
L
D
W
W
W
D
AC Milan Serie A form:
L
W
D
W
W
D
AC Milan form (all competitions):
L
L
L
W
D
L
Team News
While influential midfielder Sandro Tonali is ruled out of Saturday's game by a suspension resulting from accumulated yellow cards, Milan could have at least two players removed from their long injury list this weekend.
Divock Origi has been sidelined with a muscular problem but is now back in full training, while veteran defender Simon Kjaer may be in contention too.
However, Zlatan Ibrahimovic, Rade Krunic, Ante Rebic and first-choice goalkeeper Mike Maignan all remain unavailable to Stefano Pioli, who should recall Olivier Giroud up front following another ineffective showing from Charles De Ketelaere in midweek.
Ismael Bennacer and Theo Hernandez are among several others set to be brought back in, as the Rossoneri revert to a more familiar 4-2-3-1 formation.
Lecce boss Marco Baroni, meanwhile, will be glad to see his captain Morten Hjulmand returning from suspension, and either Alexis Blin or newcomer Youssef Maleh will make way for the Danish midfielder.
Currently on loan from Milan, young forward Lorenzo Colombo should start up front, having been directly involved in more league goals than any other Giallorossi player this season - four of his own and two assists.
Lecce possible starting lineup:
Falcone; Gendrey, Baschirotto, Umtiti, Gallo; Blin, Hjulmand, Gonzalez; Strefezza, Colombo, Di Francesco
AC Milan possible starting lineup:
Tatarusanu; Calabria, Tomori, Kalulu, Hernandez; Bennacer, Pobega; Saelemaekers, Diaz, Leao; Giroud