From TV to reality - Skippy’s path to the San Siro: “It’s been an amazing journey”

On 20 October, 2010, Oliver Skipp, aged 10, watched from home in Welwyn Garden City as Gareth Bale scored his famous hat-trick against Inter at the San Siro in the UEFA Champions League.

A few months later, he watched on TV again as Peter Crouch scored the winner in that fiery Champions League Round of 16, first leg against AC Milan, also at the San Siro.

Fast forward eight years to 18 September, 2018 and Skippy, now 18, played against Inter in the UEFA Youth League before making the short trip to the San Siro with the squad to watch a late loss against the Nerazzurri in our Champions League group opener. He made his first team debut six weeks later in a League Cup win at West Ham and, with 12 appearances under his belt, was part of the travelling squad for the Champions League Final in Madrid in June, 2019.

It all came full circle for the Academy graduate this week.

Having watched two of our iconic European moments on TV, and being there for the group stage in 2018, Skippy lined-up at the San Siro for his first start in the Champions League as we locked horns again with the Rossoneri in the Round of 16.

With midfielder Rodrigo Bentancur and Yves Bissouma injured, and Pierre-Emile Hojbjerg suspended, Skippy got his chance alongside Pape Sarr, making his debut in the competition. The pair excelled in a narrow 1-0 loss, composed and energetic a combative encounter, described as ‘a battle from start to finish’ by Antonio Conte.

It’s all set up for the return at Tottenham Hotspur Stadium on Wednesday 8 March (8pm).

For Skippy, it was a night four years in the making since his debut at London Stadium. “I remember being at school and the Champions League would be on ITV,” he told us back at Hotspur Way on Thursday. “I remember Bale at the San Siro, the 4-3 where he scored a hat-trick. Even the last game against AC Milan, when Crouch scored. I was 10, 11 then.

“Even last time we played Inter in the Champions League, I was with the Academy for the UEFA Youth League. We came to the San Siro to watch the first team game after our game, so I had experience of the stadium. It’s almost gone full circle.

“It’s crazy when you think back to it, amazing. As a youngster, you always think about that music. You try not to let your emotions get to you because if you get too caught up in it all... you can’t let it affect you, but it is amazing, the journey, and a proud moment. Obviously, I would have liked a different result, but it was a proud moment, none the less.”

After a tough 2022, where he was out for the best part of 10 months through injury having impressed in Antonio Conte’s first few months at the Club, you feel Skippy deserved a break, just not how it materialised with injuries to Rodri and Yves.

“First of all, it was horrific news for Rodri, that’s not the way you want to get into the team,” he said. “I felt ready, and I’ve been working hard to get an opportunity. Last year was tough. I felt I was playing well before that, but that happens in football. There will always be a period in your career when things don’t go the way you want them to.

“Myself and Pape in midfield, we’ve trained a lot together, we’ve had sessions together, so we’d developed a good understanding. Pape is so talented. He can do a bit of everything, and he was brilliant, considering that was his first appearance in the Champions League. We all know how talented he is, an exciting player for the future but for now, as well.

“We know the situation with injuries at the moment, so it’s a big opportunity. I’m not getting carried away with one game, I’m looking forward to the next few months, I’ll keep pushing hard and when I get the chance, I’ll aim perform like that, and hopefully better, because I feel there is more to come.”