His form continued into the 2017/18 campaign, where he scored 14 and assisted 15 across all competitions. However, arguably his best moments came at Wembley Stadium, with the first taking place in November. Just under a year on from scoring his first Champions League goal on his debut in the competition, he scored a brace and powered The Lilywhites to a terrific 3-1 win against reigning European champions Real Madrid - a side which included the likes of Cristiano Ronaldo, Sergio Ramos, Karim Benzema and Marcelo.
In April of that season, he scored another crucial goal at Wembley, this time in the FA Cup semi-final as he put Spurs 1-0 up against Manchester United, however, a fightback from The Red Devils saw Pochettino's side crash out.
Beginning of the end
The 2018/19 season is when it all started to crumble for Dele. Once a teenage sensation, the now 22-year-old was facing the first setback of his Tottenham career and had to figure out a successful way of dealing with this.
After an incredible FIFA World Cup tournament, he was expected to return to North London and deliver the goods once again, but he missed a large portion of the season with hamstring issues and only scored eight times, assisting seven goals in the process.
A rather inconsistent year led him into the palms of Jose Mourinho, who in his first few days at the club told Dele: "I understood already that you are a f*****g lazy guy in training," in front of the rest of the squad, as seen in the 'All or Nothing' documentary published by Amazon Prime Video.
However, at the start of the Mourinho era, the attacking midfielder scored four and assisted three in the first seven games, seemingly not letting his new boss' comments affect him. But, with a suspension and injury during 'Project Restart' after the COVID-19 pandemic, he found himself falling down the pecking order and out of favour.
That carried over the next two seasons, even once Mourinho was sacked towards the end of the 2020/21 campaign and under Nuno Espirito Santo and Antonio Conte when they took over in July 2021 and November 2021, respectively.
Despite being given chances in both the UEFA Europa League and UEFA Europa Conference League, his chances in domestic competitions were limited. He appeared just 25 times in the Premier League for Tottenham between September 2020 and January 2022, before he moved to Everton on a free transfer, bringing his time in North London to an emotional end.
Where did it go wrong
When Dele sat down for a heartbreaking interview with Gary Neville on Sky Sports' 'The Overlap' podcast, he spoke about the harrowing stories from his childhood and the personal struggles he faced when at Tottenham.
In the interview, which was released in July 2023, the Englishman fought back tears as he revealed that he had just come out of an American rehabilitation centre a month prior due to a sleeping pill addiction, as well as struggles regarding his mental health.
The former Spurs midfielder also discussed his traumatic childhood, which saw him adopted by the Hickford family - Harry Hickford eventually became Dele's agent, showing just how much of an impact the family had on his life.
During the conversation about his childhood, which left both Dele and Neville in tears, he revealed to the world that he was 'molested' by his mum's friend and was "sent to Africa to learn discipline, and then I was sent back." He also stated that he was smoking and dealing drugs by the age of just seven and at eleven he came inches from death when he was hung off a bridge by a man.
Recapping his time in N17, the former MK Dons youngster said that the toughest moment for him came when Mourinho stopped playing him.
"I remember I was in a bad place and I just looked in the mirror asking if I could retire now at 24 doing the thing I love. That was heartbreaking for me, to even have that thought, that hurt me a lot and was another thing I had to carry."
Whilst he said he doesn't blame anyone but himself for the downfall of his Tottenham career, there is no doubt that these huge personal issues would have taken a toll on his life, both away from football and at the club.
"I don't blame Mourinho, I don't blame anyone. My reaction to that wasn't right, but it wasn't something I had control over."
Attempting a return
Whilst things never worked out for him with The Toffees, nor on his loan with Turkish Super Lig giants Besiktas, Dele has now found his feet as he attempts what would be a spirited and sensational comeback to the very best of his game.
He joined Italian side Como in the 2025 January transfer window, a side managed by former Barcelona midfielder Cesc Fabregas and includes ex-stars such as Pepe Reina and Sergi Roberto.
If he can get back to his old levels, there will be a new monster unlocked.