Former Spurs man Harry Winks working his way back to the top with Leicester City

It may feel a long time ago now but in the summer of 2022, there was genuine excitement about what Tottenham Hotspur could achieve under the guidance of Antonio Conte. The Italian had just seen off Arsenal at the end of the previous season to earn the club a place in the Champions League for the first time in three seasons, and a number of signings that seemed to perfectly suit his rigid yet effective tactical philosophy followed.

As Conte and his players jetted off to a pre-season training camp in South Korea, it was easy to forget about four first-team players who were left at home. They were deemed no longer a part of the club’s plans for the future and were forced to train separately from those who had been their team-mates just weeks beforehand.

One of those deemed surplus to requirements was Harry Winks. The midfielder, who joined the Tottenham academy at the age of five, had made more than 200 appearances for his boyhood club by this point. Mauricio Pochettino once compared him to Xavi and Andres Iniesta, and Gareth Southgate said in 2018 that Winks was the type of player that England “wanted to build the future around”, but by the end of the 2021/22 season Conte was giving him little more than brief cameos from the bench. He went a step further in the build-up to what turned out to be a doomed campaign for Spurs and the former Chelsea boss.

It took until the final days of the transfer window for Winks to find a way out of Spurs though, as he joined Sampdoria on a one-year loan deal. An ankle injury disrupted the early months of his spell on the Ligurian coast, and by the time he was fully fit in January, the one-time Serie A champions were mired in relegation trouble. Winks received praise in the Italian press for some of his performances, but he was only able to help Samp to a solitary win in the second half of the season as they finished bottom of the league table.

During his time in Italy, Winks admitted that no one from Spurs had contacted him. It was therefore always likely that he would be on the move again this summer, and this time it was for good. Rather than trying to establish himself as part of the Ange Postecoglou revolution, the 27-year-old signed for a Leicester City side freshly relegated from the Premier League.

Despite the 10-cap England international having to step down to the Championship for the first time in his career, the appointment of Enzo Maresca as head coach at the King Power Stadium has made it a potentially career-revitalising switch for Winks.

Maresca was Pep Guardiola’s assistant at Manchester City, and he already has his Foxes playing in a manner befitting his mentor. Leicester are averaging 63.4% possession across their 14 league games this term whilst also topping the Championship scoring charts and at the same time conceding the fewest goals.

Remarkably they have won all but one of those games, with Winks starting every match so far this term. The style has suited him perfectly, with only team-mate Jannik Vestergaard completing more than his 1203 successful passes. Winks added his first goal for the club on Saturday, curling home a peach of a strike in the closing stages of a hard-fought 2-1 win at Queens Park Rangers.

“When I met the club for the first time, he was the first name I told them [to sign],” said Maresca after the win at Loftus Road. “With this idea [of playing], Harry is an unbelievable player.

“I saw him at Spurs and last year in Italy, I saw he would be a perfect player for this idea.

“Every day, on the ball and off the ball, he is trying to learn. The way he behaves is fantastic.”

The late strike was Winks’ first goal since January 2022, and it left Leicester 14 points clear of third-place Leeds United as the Foxes hunt down an immediate return to the topflight.

The midfielder from Hemel Hempstead told the club website last week that he was enjoying his football more than he has in years, and with him playing such a crucial role in a side that seems destined for Championship glory, Winks will surely be passing his way around Premier League pitches once again before long.

But given how difficult the past few seasons have been, he will surely continue to savour more afternoons like Saturday’s match-winning contribution in west London over the coming weeks and months.