When Oliver Skipp was named in the Tottenham squad for the 2019 Champions League final, he had a problem. The 18-year-old hopeful was bang in the middle of his A-Level exams. He had papers in economics and history, one before the team flight to Madrid; another shortly after the showpiece against Liverpool.
And so Mauricio Pochettino and his players would be treated to the most unusual of sights. Skipp took his books on the trip and he even did a bit of revision on the bus to the match. For the record, Skipp would get an A in economics and a B in history.
Skipp did not make the match-day 23 that night but he drank in the experience, filing it away for when he would start a major Champions League tie for Spurs. He has had to wait longer than he would have liked for the opportunity, through four appearances as a substitute in the competition, but it finally happened for him on Tuesday night – thrust into the cauldron of a sold-out San Siro for the first leg of the last 16 tie against Milan.
That Skipp was partnered in midfield by Pape Matar Sarr – at 20, two years his junior and making his debut in the Champions League – ensured the most dramatic of subplots.
The pair had started together only once previously – against League One Portsmouth in the FA Cup on 7 January – and even that was not supposed to happen. Skipp was a late replacement for Yves Bissouma, who had felt an injury in the warm-up. Apart from a couple of minutes as substitutes in the game before that against Aston Villa, it was the only time that Skipp and Sarr had shared a field.
Antonio Conte admitted on Monday night that he had no other options against Milan, having lost Rodrigo Bentancur to an anterior cruciate ligament rupture in the 4-1 defeat at Leicester on Saturday, hard on the heels of Bissouma’s foot surgery last Friday and with Pierre-Emile Højbjerg suspended. At the same time, the manager declared his faith in the inexperienced duo. He would be vindicated.
Skipp found the answers in the battle with Sandro Tonali and Rade Krunic and so did Sarr on only his third Spurs start. After Portsmouth, Conte had played him in the derby against Arsenal. Sarr, who signed from Metz in the summer of 2021 before being loaned back to the French club last season, featured in the World Cup for Senegal, coming on as a half-time substitute in the last 16 tie against England. He knows what a big game feels like.
For Skipp, it has been a journey, one that was gravely affected by injury last year. Conte had counted on him after his arrival at Spurs in November 2021 but the following January, Skipp succumbed to a pelvic problem that would end his season. It was a source of frustration for all parties, with Conte calling on the medical department in March to publicly explain why it was taking so long to heal. Skipp would suffer a foot injury in pre-season training that further hampered him.
What defined Skipp’s performance at San Siro was his intelligence in possession. The statistics showed that he completed a team high 93% of his passes and he helped to dig out a foothold after the nightmare of the early concession to Brahim Díaz, which would prove to be the only goal of the tie. Skipp moved the ball quickly and tidily, invariably getting his angles right.
It was possible to see his thunderous challenge on the Milan dangerman, Rafael Leão, in the 10th minute as the moment when he settled and the same was probably true for Sarr when he stretched to win a ball high up on 26 minutes, teeing up a shooting chance for Emerson Royal.
Sarr is the more eye-catching player and he grew into the game, stepping away from his markers to drive forward in possession; his stride rangy, his passing secure both long and short. No player had more touches, he won the ball on the ground and in the air and was not afraid to shoot from distance.
“I thought they were both outstanding,” Harry Kane said. “It’s not easy to come into that sort of atmosphere and game and perform the way they did. The boss said beforehand that we completely trust them and to go out and enjoy it. They did that.
“Skippy’s been great. Coming through the academy … he’s just a really hard worker. Keeps his head down, quite shy and gets on with his job. When Antonio first came in, he was playing a big part and looking good and his pelvic injury set him back. He’s been working hard to get his time again.
“Pape has got fantastic quality. You saw that he was everywhere – breaking up play, tracking back, making tackles, shots, crosses. He’s a player who has all the ability and he’ll only get better from experiences like that.”
Milan has its quintessential look and so do the Rossoneri, their players arriving and departing in tailored grey suits with red cuffs on one sleeve, squad numbers on the back of the jackets and matching ruck-sacks. Only in this city. Yet Skipp and Sarr more than held their own in the on-pitch style stakes and it was difficult to separate them at the top of the Spurs match ratings.
It feels as though Sarr is ahead of Skipp in Conte’s thinking, providing a better contrast to Højbjerg although, with numbers thin, both are set to be key players in the weeks ahead. Spurs face West Ham at home on Sunday. “The performances from Sarr and Skipp make me more relaxed because I know I can count on them 100%,” Conte said.
Kane took the positives in the narrow defeat, the performance a massive upgrade on the Leicester debacle, particularly in terms of the fight and control, even if a spark was missing in the final third. “We go away knowing there’s a lot to play for in the second leg,” Kane said.
When Spurs got away from San Siro, they did so without Skipp and Sarr. The pair were selected for doping control, they struggled to provide a sample and they needed to be driven separately to the airport for the flight back to London. It was a night when they had nothing left to give.
