On the opening weekend of the new season, everyone starts from scratch. Every player has a blank sheet of paper in front of them and is given the freedom to write whatever they want on it. Nine months from now, they may be looking back on the best work of their careers.
And when Tottenham Hotspur kick off their season at former club Leicester City on Monday night, no player will be more eager to start writing a new story for himself than James Maddison. Not necessarily because he’s returning to the stadium where he spent five seasons, but because for Maddison, last season was so exciting, so promising, so frustrating and so trying, with every emotion packed into that period between August and June.
Remember Maddison in August, September and October of last year, when he arrived at Tottenham and immediately started playing as if he’d been there for years? Late summer 2023, Maddison was something special. Perfect for Ange Postecoglou, perfect for Spurs. Everything went through him, and he assumed the role of creative leader, vice-captain and number 10 with amazing ease. No learning curve required. More than any other player, he embodied the excitement of a new era.
But the honeymoon period was short-lived. In November, Maddison injured his deltoid ligament and was sidelined for almost three months. It was the worst injury of his career, all the more devastating as it occurred in just his 12th game for his new club and he was in top form. Maddison was thoroughly dejected.
Maddison was injured in November (Alex Pantling/Getty Images)
It wasn’t easy for Maddison to rehab while watching his teammates play without him, but he worked hard and travelled to Dubai in December with the club’s medical staff to rehabilitate in warmer weather, before rejoining the team at the end of January. With just under halfway through the season, there was plenty of time for Maddison to find his form and help Tottenham finish within the Champions League places.
What was so frustrating was that Maddison never quite returned to his best in the second half. There were signs of this, with a neat assist for Cristian Romero in a 3-1 win over Crystal Palace in March and then a dash to score from Pepe Matar Sarr’s cross in Spurs’ 4-0 win at Villa Park later that month. With Maddison back, Spurs seemed back, with fourth place and a Champions League spot well within reach. But that was not to be seen at the end of the season.
Spurs and Maddison struggled for rhythm in the spring. Maddison was so important to Spurs that when he wasn’t at his best the whole team suffered. After heartbreaking losses to Newcastle United and Arsenal in April, Postecoglou made a decision that would have been unthinkable at the start of the season: leave Maddison out for the trips to Stamford Bridge and Anfield.
Maddison returned to the team for the final three games, but Tottenham was already far behind Aston Villa in the race for fourth place. And Maddison’s struggles would prove costly at the end of the season. He finally joined Gareth Southgate’s England squad in 2023, but although he played in the Qatar World Cup, he was injured and did not play a single minute. He then got more playing time, starting in the Euro 2024 qualifier against Ukraine in September and the friendly against Australia in October. For the first time, Southgate felt he could rely on him. And even after his struggles, Southgate selected Maddison for the Euros’ 33-man extra squad. Maddison came off the bench in the warm-up game against Bosnia and Herzegovina at St. James’ Park.

Maddison played against Bosnia but was left out of England’s Euro 2024 squad (Mark Atkins/Getty Images)
But three days later, Southgate was forced to cut seven players from his squad to Germany, with Maddison missing his flight. “Devastated is an understatement,” Maddison wrote on social media. “My form at Tottenham, coming back from injury in the second half of the season, was probably not at the level I set for myself and that has forced Gareth to make the decision.”
It’s surprising that a season that started so well for Maddison should end in such a sour way – he had the world on his hands for the first few months and the step up from Leicester to a ‘big six’ club looked like child’s play.
Throughout his career, Maddison has been hailed as one of the most talented English players of his generation. All the big clubs knew him from his days at Coventry City. Scouts from Barcelona came to watch him play for Norwich City at Carrow Road. And in his first few weeks at Spurs, it felt like Maddison was fulfiling his potential and becoming the player he was meant to be.
However, given how this season has played out, it looks like Maddison will have to work hard again. He is still first choice, but there may be more competition for the left centre-midfield position this season. Dejan Kulusevski is both a winger and a midfielder for Postecoglou’s Spurs. And then there’s the excellent 18-year-old Lucas Bergvall, who recently joined the club. If he performs (probably in the Europa League), there will be more calls for Bergvall to play more often. And Spurs could still look to add another centre-midfielder in the final two weeks of the transfer window, just as they did in June when they tried to sign Jacob Ramsey.
But there are reasons for optimism. We know how good Maddison can be in the system, how much he wants the ball, how good he is at finding space and making clever passes to Son Heung-min. The addition of Dominic Solanke, Maddison’s good friend, could provide him with a new target man and boost the whole team. Maddison can also damage opponents from set pieces and on the edge of the box. We’ve all seen how good Maddison can be for Spurs. The challenge for Maddison, and for Tottenham, is to translate what started last season into what this season has been all about.
(Top photo: Andrew Milligan/PA Images via Getty Images)