The Italian will allegedly replace Tim Sherwood at the conclusion of the current campaign, as revealed in Corriere dello Sport (via Ben Jefferson of the Express):
Allegri was sacked by Milan in January and has reportedly been living in London since that time in a bid to learn English in preparation for a Premier League job.
And Italian daily Corriere dello Sport claims that Daniel Levy is ready to offer the 46-year-old that opportunity by replacing Tim Sherwood at White Hart Lane.
Jefferson's report suggests current Milan assistant Mauro Tassotti will join Allegri on his London adventure, while James Horncastle of BT Sport posted the original front-page headline:
However, ESPNFC's Kevin Palmer reports that other sources are denying Corriere's report on the former Milan manager:
Former AC Milan boss Massimiliano Allegri is not being lined up to be the next Tottenham head coach, sources at the North London club have told ESPN FC.
Allegri has been out of work since he was relieved of his duties at Milan in January, while he has previously expressed an interest in working in the Premier League.
And Corriere dello Sport claimed on Friday that the Italian will "officially become the coach of Spurs."
However, sources at Tottenham have told ESPN FC that "'the story is rubbish," denying that the Italian is in the running to replace Tim Sherwood -- who is widely expected to leave in the summer -- and insisting that no negotiations have taken place.
Earlier this month, Daniel Levy spoke on the state of Tottenham, courtesy of the Guardian:
We have come far in the last decade – we have raised our expectations from a club aiming to be in the top half of the table to competing in Europe each season – to the point at which we find ourselves disappointed if we don't make the Champions League.
This season, we have had to make significant changes, both in coaching and playing staff and yet we are currently only two points less than last season's tally. Whilst this season's performances and results have not lived up to expectation, we believe our squad has potential and it is important that we all now show commitment and teamwork to get the best possible finish to the season.
Despite recent troubles at Milan, Allegri has enjoyed plenty of success throughout his managerial career. A 2007-08 Serie C1-winning campaign with Sassuolo, who now reside in Italy's top flight, provided the backdrop to further progress made at Cagliari.
Allegri led a limited Rossoblu side to an impressive ninth-place finish during the 2008-09 season but exited his role in April 2010, with Cagliari down in 12th. He soon joined Milan where he won the Serie A title and Italian Super Cup during his first season.
Since then, Allegri's success has stalled. Juventus have managed to reassert their dominance atop Italy's domestic division and are on course to win their third straight title this year. Milan lost out by four points during Allegri's second season in charge, 15 the next and are currently 39 points behind Antonio Conte's leaders.
Ironically, Milan dismissed Allegri after suffering a 4-3 defeat to Sassuolo in January—the club he helped set in motion, per BBC Sport.
Allegri's potential appointment at Spurs would serve up little surprise. Daniel Levy's affinity with chopping and changing managers never ceases to exist, while under-pressure technical director Franco Baldini may receive a smidgen of extra leeway if his countryman is installed.
Baldini "must take his share of the blame" for Spurs' recent failings, per Jamie Redknapp of Sky Sports. Tasked with replacing Gareth Bale, both Levy and Baldini have failed to land players who can consistently improve Spurs' chances of Champions League football. Indeed, as the current team struggles in sixth, it seems progress has taken a backward step.
The Mirror's David Kidd believes Baldini's future is in doubt, but he could be given extra time to prove his worth if Allegri is installed. It is likely the potentially incoming Italian will wish to keep his compatriot in North London, especially during the teething process of his tenure.
Although Allegri has proved quality throughout his managerial career, Spurs fans may be disappointed to hire a coach with a recent history of failure. His reputation also pales in comparison to Louis van Gaal and Jurgen Klopp, who are both linked with Spurs, as reported by James Dickenson of the Express.
Whoever the appointment, Levy can't afford to get his next managerial selection wrong. Supporters have witnessed their board wade through bosses in recent times—with three different leaders in as many years—and will want to see some longevity at the club.
Allegri would be a low-key hire considering the other names linked, a result in keeping with Levy's tenure at White Hart Lane.