Dele's fortunes would gradually deteriorate following Pochettino's sacking in November 2019, with injury problems and middling form causing him to slide completely out of favour as a succession of managers - including Jose Mourinho and Antonio Conte - passed through what became a revolving door at the Tottenham Hotspur Stadium, before he was allowed to join Everton on a free transfer in January 2022.
In May 2020 at the height of the Covid-19 lockdown, Dele was held at knifepoint and physically assaulted in his own home in north London during a burglary. Tottenham fan and journalist Sean Walsh believes that was a watershed moment in his career. "I don't think he ever got over it," he tells GOAL. "In Project Restart we barely saw him, he didn't really play. Then 2020-21, that whole season basically he's just a non-factor, he's not there, he's not playing. It was a slippery slope and he just never got back into it."
Throughout his career, Dele had been battling demons as well as form and fitness. In a candid interview with Gary Neville on The Overlap in the summer of 2023, he shed light on the trauma of his childhood, revealing that he had been sexually abused aged six and had been exploited to deal drugs by the age of eight.
He also opened up about his mental health issues and an addiction to sleeping pills, which led him to spend six weeks in a rehabilitation centre earlier that year following his injury-impacted loan spell at Besiktas. It was around that time that photos were published that appeared to show Dele inhaling laughing gas. Earlier this year, the Daily Mail reported that he had lost £150,000 "in a matter of days" in late-night card games at a London casino.
"Don't get me wrong," he told Neville. "I love football, it saved my life, I owe everything to football. But it's not just as easy as everyone thinks it is. It's not this 'high life'. Yes, you have money, you can do a lot of things that you wouldn't be able to do without it. But mentally, I don't think people will ever understand until you're in it, what it can do to you."
On his return to England, Dele was sidelined by a series of injuries for an agonising 18 months, missing the entire 2023-24 campaign. Despite his contract ending in the summer of 2024, he worked his way back to fitness with the help of Everton's medical staff before securing a free transfer to Como in January 2025.
However, the England international has been without a club since leaving the Serie A side by mutual consent in September 2025, shortly after his split from girlfriend Cindy Kimberly, where he infamously made just one nine-minute cameo before being sent off for a reckless foul on AC Milan's Ruben Loftus-Cheek.
That remains his most recent competitive appearance at the time of writing, 19 long months ago. Since leaving Tottenham midway through 2021-22, Dele has only featured in 29 matches. Thirteen of those came at Everton, another 15 on loan at Besiktas, and then the solitary appearance for Como.
Dele has spent the past year training independently, sharing semi-regular updates on social media, and two transfer windows have now passed without him finding a new club. At this stage it's unclear where, when or even whether his playing career will resume. Finding himself with lots of free time on his hands, he has turned to streaming on Twitch. It's a move that has divided opinion.