Tottenham Hotspur host Gillingham in the League Cup on Wednesday evening, and Mauricio Pochettino has a decision to make. His senior players are still finding their feet, but he has a new set of young players fighting for inclusion in the first team. None has made a stronger case than Harry Winks, the local boy midfielder. He has made four first-team appearances so far, including his Premier League debut off the bench on 27 August. But this week he is in contention for his first start.

For Winks it would be the most important marker yet on a journey that has already taken more than half of his life. Winks joined the Tottenham academy at the age of eight, and he is now 20 years old. He is a Tottenham fan, because his parents Gary and Anita are. He is from Hemel Hempstead, and of the current squad only Harry Kane from Chingford and Josh Onomah from Enfield are from stronger Tottenham places than that. He is precisely the type of young player the club wants to develop.

Winks is also the type of player that the club is best at developing. John McDermott’s Tottenham academy, with its emphasis on technical skill and one on one situations, has produced plenty of very gifted youngsters over the last few years. Winks has always stood out, from when he captained the under-18s and before, for his passing and control of the game.

The challenge for Winks, as well as for the next generation talents of Marcus Edwards and Shayon Harrison, is to prove that they are ready for the very different demands of Mauricio Pochettino’s first team. But Winks has been giving himself the best possible chance to do that, through his hard work and his professionalism. And Pochettino has noticed.

Pochettino has an unusual policy when it comes to bringing through young players, a policy which he took from Southampton to Tottenham. He is a hands-on coach with a clear philosophy of the game. If he rates a young player, he does not want that youngster to be coached by anyone else. He wants to make them as good as he possibly can through his hard working on the training field. If, then, they are not good enough for his first team, then they can leave. But Pochettino wants to find out for himself.

That is why Winks is 20 years old but has still never been on loan. There has been plenty of interest in him in the past, and this summer Barnsley, Reading and Brighton were all hoping to take him into the Championship. But Pochettino said no and last week Winks signed a contract at Spurs until 2021.

That was partially a reward for a summer in which Winks made a serious impression on Pochettino and his staff. He has always been a driven goal-oriented youngster, and knew that this season would be the most important of his career. When he arrived back for pre-season club staff saw that he was quicker and stronger than ever. He went to Australia and was Spurs’ best player when they lost 1-0 to Atletico Madrid side, seven of whom started the Champions League final two months before. He impressed against Juventus too, and put down a marker for the season.

Every 20-year-old wants to play games and Winks is no different. But he would not have stayed at Spurs if he did not trust in Pochettino’s plan. There is a trade-off between guaranteed game time and technical development, and while this season Winks is set for the latter, the opportunities will come.