Former Chelsea and Italy midfielder Roberto di Matteo is the latest Premier League legend to reveal all to the MOTD Top 10 podcast.
Di Matteo was a two-time FA Cup winner with Chelsea, making more than 150 appearances between 1996 and 2002, before taking over as manager of the Blues in 2012.
He led Chelsea to victory in the Champions League and FA Cup final in his first year as manager.
The Italian joined Gary Lineker to reflect on the moments and people that shaped his playing career.
Best player you have played with?
“Paolo Maldini. He was a modern footballer in the 90s. At the time, he was a fantastic, physical specimen. He was fast, technically very good and tactically so well schooled.
“It was a joy to play with him in the team and to be around a motivated person like him. He used to lead by example. You grew up with the art of defending in Italy.”
Best player played against?
“One was the Brazilian Ronaldo. He was in his early twenties and we played against Brazil in France a year before a World Cup.
“I was just so impressed. Everybody knew of him, of course, but you couldn’t get near him on the pitch. He was just so quick and so strong. Ronaldo with the ball was quicker than Maldini.
“Thierry Henry was the other one. He was powerful and very clever. He was one of those players who would get into the space and between the lines.”
Best manager played for?
“I had one in Switzerland that nobody would know. He taught me so much about the tactical understanding of the game. His name was Rolf Fringer. We [Schaffhausen] won the league under him in 1993 with a small team.
“Then there was Arrigo Sacchi who took me to the next level with Italy. He was very intense. We used to hide in hotel rooms because he would knock on players’ doors to have a chat and continue to teach you about tactics. We would switch our lights off at nine o’clock to pretend we were asleep.
“Ruud Gullit was also very good. He brought me to Chelsea and was just so relaxed. Nothing would fuss him.”
Favourite goal scored?
“It was probably my goal in the FA Cup final in 1997. Not just because it was a good strike but also the importance of it which led to more trophies and playing in international competitions.
“It was my first final and I remember Gullit just being so relaxed the night before. I lost my head in the celebration.”
Favourite game played in?
“One of the Rome derbies. The intensity and the lead-up to the game… the whole town was electrified by this game. You can’t go out of your house. Everybody is on you to win the game. They are the best games you can be involved in – especially if you win them.”
Footballing hero growing up?
“I was 12 years old when Italy won the World Cup in 1982 so my childhood heroes were Bruno Conti and Paolo Rossi.”
Funniest moment during career?
“We signed Marcel Desailly in 1998 for Chelsea and he had just won the World Cup and European Cup.
“We went to play Manchester United in March and Marcel looks around and sees Jesper Blomqvist – of course, they played together in Milan. So he shouts: ‘Jesper, you are here now.’
“He had been there for nine months. That was how much he was aware of what was going on in football…”
‘What if’ moment of your career?
“I had a chance to sign for Lazio again and to go back. They won the league in 2000 and Sven-Goran Eriksson was the manager. He really wanted me.
“I also had a terrible injury with all the complications and that is what killed me in the end. Bones can grow and recover but soft tissue is different. I had just turned 30. I was feeling good.
“It was probably the worst time in my life after the injury. When you look back you realise, I really did suffer mental health issues.”
Craziest team-mate you played with?
“Paul Gascoigne. I joined the club at the age of 23 from Switzerland. I did some work with the physio after a training session so was late leaving.
“I walked over to the car. I was looking at it and thinking the wheels don’t look right. He had deflated all of them.
“He was so much fun. Because of his personality and character, he used to deflate the nervousness of the team. He used to bring a really good atmosphere to the team. It was a joy to play with him.”
Favourite international moment?
“It was probably in the European Championship in 1996. We played at Old Trafford against the Czech Republic in the first game. At the time, England had nice stadiums compared to the rest of Europe and especially to Italy.
“It was a big competition for me and we played well. That was one of the best experiences that I had internationally.”
