The midfielder has endured a frustrating period since suffering a cruciate ligament injury in August 2025, which kept him sidelined for almost the entirety of last season.
A shoulder problem at the start of the current campaign then delayed his return to full fitness, leaving him fighting to regain momentum at a crucial stage of his career.
There were very encouraging signs in his first Premier League start of the season against Coventry City, when he scored in a 3-1 victory. It was an important moment for a player who has had to show considerable patience and determination to get back to where he wants to be.
Sources say Maddison is displaying an impressive will to overcome setbacks, with a very strong desire to prove he can still be an important player for Tottenham.
There is a sense that he is approaching this period with renewed motivation, aware that he needs to turn his return to fitness into consistent performances.
At 29, Maddison still has time to make a significant contribution - but his contractual situation adds another layer of importance to the season.
His current deal runs until June 2028, meaning the coming campaign will be significant as he moves towards the final 18 months of his contract.
Maddison aims to earn an extension rather than leave questions over his future unanswered. To do that, he will need to demonstrate that he can stay fit and influence games regularly.
His quality has never been in serious doubt, but availability has become the major question after such a difficult run of injuries. If he can put that behind him, he could become a catalyst for Tottenham's season, bringing creativity and experience to a side that needs its influential players firing.
For Maddison, the challenge is now to turn determination into sustained performances. A successful comeback could strengthen his position at Spurs and give him a genuine platform from which to earn the new contract he wants.
Dean Jones has been a transfer news and football insider for Flashscore since 2025, as well as a journalist for leading UK newspapers and websites over the past 20 years, establishing himself as an authoritative and trusted voice in the industry.
