Still just 30 years of age, the former England international, arguably one of the most gifted players of his generation, is hanging on to his football career by a thread.
Personal problems
No football fan could've failed to have been moved by the emotional interview that the player gave to English media back in 2023, where he detailed the issues he had faced in his childhood, which had largely contributed to his wayward life off the pitch.
Ultimately, the mental trauma that he has had to deal with as a result of that has taken its toll on the way in which he earns his living.
Multiple injury concerns, subsequent lack of rhythm and the associated lack of confidence that then comes from not playing consecutive matches, have also all contributed to ensuring that Dele has played just 37 league games since 2021.
That he is even able to motivate himself to earn a contract after so many setbacks shows great courage and determination, which the player will need if he is to finally end his personal hell once and for all.
Just nine minutes played for Como
Having spent time at Everton and Besiktas, Dele's last playing destination was at Serie A side Como, managed by Cesc Fabregas.
After having signed on an 18-month deal in January 2025, it wasn't until March that he made his debut for the club against AC Milan.
However, any joy at being back on the pitch after a two-year hiatus was short-lived.
Arriving in the 81st minute as a late substitute for Lucas Da Cunha, Dele was subsequently sent off 10 minutes later for a trip on Ruben Loftus-Cheek, and that was the last time that he kicked a ball in anger for Como before being released.
Unable to find a club for the entirety of the 2025/26 season, he has effectively played only nine minutes of senior football since February 2023.
Therefore, any club willing to take the player is clearly doing so with huge risk attached.
Monza could make a move
That hasn't stopped Monza making enquiries as to the possibilities, given that Dele is a free agent and so would therefore come at no cost other than an agreed salary.
Monza are back in Serie A one year after being relegated, and for what will be only their fourth season in the Italian top-flight in club history.
Ivan Juric is the manager charged with ensuring that I Biancorossi can consolidate in the 2026/27 campaign and continue to progress as an elite outfit, and it's expected that he would have the last say on whether Dele is worth taking a punt on or not.
It's understood that the Englishman has kept himself fit during the year that he's had out of the game, though there's clearly no substitute for match fitness.
Dele still has a point to prove
Of course, Dele is only going to achieve that by being given the opportunity to play games and get up to speed both in a physical and mental sense.
Given what he's been through already, no one would begrudge him the chance to make a success of a comeback that would arguably be amongst the best for any sportsman or woman to have achieved.
Unfortunately, football is rarely about sentiment, and for a team that might well be considered one of the favourites for relegation back to Serie B (they opened their 2026/27 account with a 4-1 defeat at Internazionale), Monza can't afford to take any chances, free transfer or otherwise.
They will understand, however, that if they're to get a player free of the shackles, he can still be a difference maker.
With a point to prove, too, there's no ceiling on what Dele could achieve over the course of the next 12 months.
There's only a week left of the summer transfer window, though, so the Italian side don't have long to decide whether to offer him a year's contract, with a year option, as has been mooted. Time is of the essence if they want to get a deal over the line.
For the 30-year-old, it could represent the final chance of his football career, and an opportunity to end it in the best possible way - on the pitch.
Jason Pettigrove has been the features writer for Flashscore since 2025, utilising Opta data to form the basis of his articles. He has previously worked for high profile football clubs, news and media outlets, both in print and digital, and can usually be found watching FC Barcelona when time permits. You can read more of his pieces here.
