Spurs remain winless in the Premier League after six matches, but produced an impressive display in Saturday’s 1-1 draw at Manchester United – where Maddison was used off the bench for a fifth time this season.
The 29-year-old has struggled to get back to full fitness after two serious knee injuries in 2025, including a rupture of his anterior cruciate ligament, but Stevens, who was academy manager during Maddison’s time at Sky Blues, believes the playmaker can become Tottenham’s difference-maker again.
Ahead of Coventry’s trip to Spurs on Monday, Stevens told the Press Association: “His driver is, ‘am I playing 90 minutes and can I go and score some goals and ignite the fans,’ you know? So this injury would have hurt him a lot.
“Even in a 10-minute spell (now), when he comes on, he takes the ball and he makes things happen.
“He makes things tick and he gets the team playing forwards. He gets the team moving up the pitch.
“And good grief, Tottenham have had a tough time. They’re an unbelievable football club and you know the players they have, maybe he’s the bit that’s going to connect everything together.
“I hope he’s going to return and he’s going to connect everything together for Tottenham because I think he has that ability to do that.”
Stevens watched 52 youth prospects make their full debut for Coventry during 12 years in charge of the academy and can remember how a young Maddison “ran that group” to ensure certain standards were met.
Coventry’s financial plight more than a decade ago opened the door to youth-teamers and despite being sent off in his 12th appearance, Maddison grasped his chance and scored in a final day win at Crawley which kept his boyhood club in League One. Four years later and he had played for England.
Tottenham were interested in Maddison in 2016, but had to wait another seven years to secure his services and a rollercoaster spell in N17 has followed of 83 appearances, one Europa League triumph and a nervy relegation battle.
Ahead of Maddison’s third meeting with Coventry, Stevens can still recall the diminutive midfielder that caught the eye on his first day.
“James was under-11. We were away at MK Dons and there was this pitch behind me and there’s this little fella who just kind of carried the ball and twisted and turned,” Stevens said.
“We knew he was a good player. Every team we ever played against were always aware of him and they knew him. And, I’ve said it many times, he just loved football.
“Loved football, obsessed with it and no surprise he has had the career he’s had.
“If you see those pictures of that 2014-15 season, he does look like a boy, but he might have been a boy in his body, but he certainly wasn’t a boy in his mentality, in his understanding of the game and his courage.
“That goal at Crawley that year, the club were 20 minutes away from a pending relegation. And I remember he arrives in the penalty area and he punches one bottom corner.
“Local boy, lives 300 yards from the academy training ground… you couldn’t have wrote a more apt script really.”
Coventry fans only enjoyed Maddison for 42 appearances, but he can expect a special reception on Monday.
“He hasn’t changed,” West Brom academy boss Stevens insisted.
“He came into his box after a game (in 2024), jumped over the sofa and we’d not seen each other for two or three years. And it was like he’d never been away.
“You don’t forget that. That’s a boy that is really appreciative of all the things that staff of Coventry did for him.
“Everybody’s really proud and Coventry will be proud as well. They’ll be looking forward to playing against him, I’m sure.”