An interview with Teddy Sheringham, by Callum McFadden for WFi.
You started your career at Millwall and had loan spells at Aldershot and in Sweden. What were those early years like for you, in terms of your development, especially since you broke into first-team football at such a young age?
“I made my debut at 17, but my managers felt I wasn’t quite ready to be a regular, so they sent me out on loan – first to Aldershot, then to Sweden. At the time, I wasn’t happy about it. I thought I was ready, but looking back, I clearly wasn’t.
“Playing in Sweden was a big step forward. We were in the second division, won the title, and got promoted to the Allsvenskan. It was proper men’s football – playing for points and playing for wages that people relied on. It was a big contrast to reserve games and friendlies back at Millwall. It made me grow up fast.”
When you returned to Millwall, you struck up a really effective partnership with Tony Cascarino. What was it like playing alongside him?
“It worked really well. A lot of people said it wouldn’t because we were both big lads up front, but we were determined to prove them wrong.
“Back then, centre-halves wanted to bully you, get tight, and dominate. When Tony came in, he’d attract the bigger defenders, and I’d often get the smaller ones, so we found space and balance between us. The style of play suited us too – direct, quick, and with good service from the wings. We thrived on it.”
You then moved to Nottingham Forest in the final season of the old First Division. That season saw a top-eight finish, a League Cup final, and you scored the first-ever live goal shown on Sky Sports in the Premier League era. How was that period for you?
“It was a brilliant time. At Millwall, I’d played with very good players, but at Forest, I was surrounded by top players such as Des Walker, Stuart Pearce, a young Roy Keane, Nigel Clough, and Ian Woan.
“These were international-calibre players, and the standard was higher. And of course, playing under Brian Clough was an experience in itself.
“He had his own unique ways, and it was fascinating to learn under someone like that early in my career.”
You also played for Sir Alex Ferguson at Manchester United. How did his style compare with that of Brian Clough, and how do you reflect on your time at United overall?
“I was 31 when I joined United, and by that point, I’d already had five brilliant years at Spurs, which I’d say were my prime.
“But at United, I was surrounded by world-class players across the entire squad, and working under Sir Alex was something special. He just knew how to get the best out of people.
“He understood how to motivate individuals and the team. I was lucky to work under some fantastic managers, but Sir Alex had something extra.”
Despite joining United later in your career, you won Footballer of the Year and played a key role in the treble season. Is that something you take particular pride in?
“Definitely. Everyone peaks at different times. Some players like Wayne Rooney or Michael Owen come into the game and shine from day one.
“For others, like me, it takes longer to understand your game and find consistency. I hit top form a bit later, but to contribute to the treble and win individual honours at that stage made it all the more rewarding.”
The 1999 Champions League final is one of the most iconic moments in football history. Trailing to Bayern Munich in injury time, then you score an equaliser, then Ole Gunnar Solskjaer scores the winner – how often are you asked to reflect on that night?
“Honestly, I’m reminded of it every day. Someone always brings it up – telling me where they were, what they were doing, how they felt. It’s one of those moments that sticks with people. It looked like we were beaten, and then we turned it around in stoppage time.
“To this day, people come up to me and say that by the time they had finished celebrating the first goal, we’d already scored the second. Fans in pubs were still reacting to replays of my goal when Ole scored the winner. It all happened so fast and still feels almost surreal.
“I have never celebrated so long on a pitch. We must’ve done three or four laps of honour. But it wasn’t just about that night or the Champions League – it was a release of emotion from the 11 days before that, winning the Premier League and the FA Cup.
“Looking back, I am very proud of not only how we won the Champions League but how we completed the treble in the manner that we did – it was unforgettable. That’s why people want to talk about it so much. It means something to everyone.”
You had two spells at Tottenham and are now in the club’s Hall of Fame. What does Spurs mean to you?
“It means a lot. I was released by Tottenham at 14, so to return years later as a £2 million signing — which was a lot of money at the time — was quite a moment. I knew the club well already, and I absolutely loved playing there. The fans, the atmosphere, everything about it was special.
“After four years at United, it made total sense to go back. I still hold those memories close.”
In the final years of your playing career, you featured for Portsmouth, West Ham, and Colchester – still scoring goals well into your late 30s. Was it your love of the game that kept you going?
“Absolutely. At Portsmouth, Harry Redknapp looked after me in terms of training. Then Alan Pardew did the same at West Ham. It’s not like I was dodging sessions – I trained properly – but you do need to manage your body differently at that stage. I was lucky I didn’t suffer major injuries.
“I still felt fit and effective. I loved the game, and if clubs still wanted me, I was more than happy to keep playing. I was being paid to do what I loved. Why stop?”
One thing you were always praised for was your footballing intelligence – knowing when to move, when to hold your run, when to find space. Was that instinctive, or did it develop over time?
“It definitely developed. Early on, I was the main centre-forward. But around 26 or 27, I started playing with different types of strikers – some big, some quick – and I realised that by dropping into pockets of space, I could be more effective. Playing with someone like Jürgen Klinsmann helped too.
“Defenders were so focused on him, and that gave me space to operate. I still got in the box to score goals, but my overall game evolved.”
You also earned over 50 England caps, scoring eleven goals, and then went into coaching and management. Do you ever think about returning to that side of the game?
“I’m very happy with my life now. I don’t want to go back into that rat race where there is little time to implement your ideas.
“Despite that, I am really glad I did it because I loved coaching and managing, but the noise that comes with it behind the scenes is something I do not miss in the slightest.
“It didn’t last as long as I would’ve liked, but I got a real understanding of what managers go through.
“When someone like Ange Postecoglou loses his cool with the press, I get it. I know where he’s coming from. But I’ve done my bit, and I’m happy to be out of that pressure now.”
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