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With a football career that spans a quarter of a decade and includes an impressive 51 caps for England, Teddy Sheringham MBE certainly has a lot of airmiles under his belt from his international fixtures alone. Couple that with his love of playing golf around the world and spending time on holiday with his family and we certainly had a lot of football and travel talk to get through…

In a rooftop apartment in Rome
Starting at the beginning, Sheringham’s remarkable career commenced at Millwall where he scored 111 goals and still holds the record for being the second all-time leading scorer. And it was his time at the club that Teddy cited as being among his top career highlights. “Getting Millwall to the top division for the first time in the club’s history was fantastic as a young player,” he says. “Playing for Tottenham Hotspurs after being released by them as a kid was a massive moment too and so was the entire Euro ’96 tournament. But probably the icing on the cake was winning the treble with Manchester United in 1999, culminating in winning the Champion’s League final and having a hand in both goals. All the celebrations in Manchester will live with me for the rest of my life,” he reminisces. 

Waiting to play for England with the old boys in Germany, Ray Parlour and Paul Merson
Football was always the plan for Sheringham; “I had no backup. I’m very lucky because I wouldn’t have had a clue what to do if I wasn’t a footballer,” he says. “To get paid to play football – even from a young age when it was only 100 quid a week – was amazing. So, to play for the top clubs in the world, as I see it, and end up winning trophies, was just beyond my wildest dreams. Being paid to play football for 25 years is probably my biggest highlight.”

Latest trip to Dubai with good friends
His career wasn’t all silverware and smiles, as Sheringham famously fell out with Spurs owner Lord Sugar back in 1998. So just for the Tottenham fans out there, we asked if he would have stayed at the club if it wasn’t for this disagreement. “I probably would have done,” he says. “But it wasn’t just about money. I wanted assurances that the club was going to buy good players again. At that stage of my career I wanted to play with the best players in the country and in the world, and it didn’t seem like Tottenham was going to be doing that, so that’s where the row with Alan Sugar came in.”
At Meydan Races in Dubai
Of course, being on the pitch for over two decades comes with some lows as well as the highs, and Teddy recollected his number one disappointment that still haunts him today. “I was playing for West Ham United in the FA Cup final against Liverpool. I was very good with my head and scored a lot of headers in my time. But this particular cross, all I had to do was flick it off the side of my head and it would have gone inside the post. But I missed and inevitably the game went to penalties, and we lost. If I had just done my normal flick we would have scored and probably gone on to win the cup.”

But the lows were always drowned out with the highs, which is why Teddy received an MBE in 2007. “It was for my services to football that got an MBE. It’s quite surreal really. All that time I was playing football and getting paid quite handsomely for it, and all of a sudden I got an award for it. But it was a fantastic day at Buckingham Palace. It’s a shame the Queen wasn’t there but I did meet Prince Charles.”

Horse riding at Chewton Glen
We couldn’t talk football without discussing locker room antics. “I remember being in the Manchester United dressing room when I had just joined the team. We were coming in after a cold day training and were all jumping in the shower and Peter Schmeichel - the then goalkeeper - was standing there drying his hair. Nicky Butt was in the middle of the changing room but he was stirring a big tea urn with a spoon, so that everyone could warm up with a cuppa. It was a massive pot. 

“So Nicky Butt was stirring the tea and he was looking a Peter while he was drying his hair and everyone could see what he was thinking: That he was going to burn him. In the football dressing room you burn someone on the back of the arm or the back of the neck, but when someone is standing there fully naked, drying his hair and can’t see what he’s doing… you could tell exactly Nicky was thinking. ‘I’ve got to haven’t I?’. He’s looking at us and were going ‘you couldn’t, you aren’t going to are you?’ And the next time Peter went to dry his hair, and put his towel up around his head, Nicky burnt the end of his manhood with the spoon, then absolutely scarpered and Peter Schmeichel was chasing him all round the changing room,” he laughed.  

Dubai celebrations
Away from the pitch, Teddy is a keen golfer and successful poker player. “I played a lot of cards throughout my childhood with my mum, dad and brother and we’d also spend a lot of time on coaches playing Three Card Brag and Kalooki. Then poker came around and started getting big in this country, so I began playing it more. It was a good way for me to indulge my competitive side and enjoy the excitement of winning when I finally hung up my football boots.

“But golf is a huge passion of mine,” he continues, and one which goes hand in hand with his love of holidays. “My clubs always seem to come with me. It’s me, my wife, our three young children and my golf clubs… I’m not sure which I love the most,” he jokes. His golfing pursuits have taken him to some of the most beautiful areas of the world from the Scottish Highlands to the stunning emirate of Dubai. 

About to play Sage Valley on Augusta with my eldest Charlie
When discussing where’s number one on his bucket list, golf was again at the forefront of his mind. “I want to play Augusta National in America where they play The Masters,” he explains. “And I want to play it before I get too old and not fit enough to enjoy my round.”

Carrying on our talk of travel, Teddy revealed that his favourite city is Rome. “I just love the way that the Italians are so passionate about their city. The way they talk with so much pride is just beautiful. I’ve been a few times, mainly for football, and it’s also the spot where I got down on one knee and asked my wife to marry me.”

One&Only Dubai with one on the way
But non-surprisingly, when asked where he would love to visit first if he could pack his bags and jump on a plane tomorrow, golf as well as his family was key to his decision. “Years ago when I was in Manchester, my next door neighbour sold his business for untold amounts of money. He hired a plane for him and his best friends, their wives and families - I think there was about 50 of them in total - and they travelled for a couple of months, playing golf, enjoying great dinners. I mean, that sounds the absolute dream to me.” 

He’d start off in Japan after his family enjoyed the sights during the 2002 World Cup: “I was coped up in a hotel room preparing for the next game, but they loved every minute of it, so I’d have to start by going back there” and of course would book his travel through Winged Boots. “Because, if there were any problems, which there often are with airline changes and hotel check-in, or if you’re not happy for whatever reason, Winged Boots does its upmost to sort things out as quickly and as cost-effectively as they can, and I thank you very much for that,” he concludes.
Lauren Godfrey

Lauren Godfrey is a Marketing Manager


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