The former Leicester City playmaker took North London by storm upon his arrival in the summer window, amassing three goals and six assists from his opening 11 Premier League appearances.
With Maddison pulling the strings in the number 10 role, Tottenham accrued 26 points from their opening 10 top-flight games of the new term, representing a managerial record for the newly-appointed Ange Postecoglou.
However, injury cruelly struck for Maddison during Spurs' showdown with London rivals Chelsea on November 6, as he twisted his ankle while sliding on the turf and had to come off just before half time.
Postecoglou immediately admitted that the 27-year-old's concern was as severe as it looked and ruled Maddison out until the New Year, and his absence - alongside that of several others - coincided with Tottenham's dip in form.
Following Maddison's enforced withdrawal against Chelsea, Spurs were subjected to a 4-1 humbling in their first top-flight loss of the season, and they have only won four of their subsequent 10 Premier League fixtures without the playmaker.
Postecoglou has been loath to put an exact date on Maddison's comeback, but he expressed optimism that he would be back with the group before the end of the month, and Tottenham have now announced the Englishman's return to practice.
In two separate social media posts, Tottenham shared an image of Maddison lacing up his boots with the caption "Look who's back" before posting a second picture of the midfielder on the training pitch.
Postecoglou will be expected to provide an in-depth update on Maddison in his press conference later this week, but the ex-Leicester man could be in contention to make his long-awaited comeback in Friday's fourth-round tie with the holders.
Earlier this month, it was also reported that Manor Solomon was targeting a return against the treble winners after undergoing a knee operation in early October, which has ruled him out of Tottenham's last 15 matches in all tournaments.
However, Spurs fans remain in the dark about the Israeli winger's condition, and all of Dane Scarlett (unspecified), Giovani Lo Celso (thigh), Ben Davies (thigh) and Alejo Veliz (knee) will miss the visit of Man City.
Furthermore, Mali's Yves Bissouma and Senegal's Pape Sarr will both be competing in the Africa Cup of Nations knockout rounds later this month, while Son Heung-min is gunning for Asian Cup stardom with South Korea.
Additional fitness boosts could still arrive in the shape of Dejan Kulusevski and Ryan Sessesgnon, though, with the former expected to return from the illness which kept him out of the 2-2 draw with Manchester United on January 14.
Meanwhile, Sessegnon made his first appearance of the season in the third-round beating of Burnley after a summer thigh operation, but a "slight niggle" meant that he was unavailable to face the Red Devils.
Postecoglou also played down Micky van de Ven's late withdrawal against Man United as cramp-related, but Radu Dragusin is on hand to make his first Tottenham start should the Dutchman be spared against Man City, who have been beaten in all five of their previous trips to the Tottenham Hotspur Stadium without scoring a single goal.