David Ginola [Photo: Jav The_DoC_66]

The Best Tottenham Wingers You’ve Seen Playing – Team Selection

It’s into midfield with Team Selection. The goalkeeper and defenders have been selected so it’s wide midfield and your choice of the best wingers you’ve seen playing for Tottenham since the 1950s. There are some excellent players to choose from although the role has changed over the years.


Tottenham have had an abundance of talented wide midfield players or wingers throughout their history. Back in the early days, Tottenham’s first FA Cup winning teams owed much of their success to their wingers who were capable of taking on a defence, providing accurate crosses and scoring some important goals. The 1901 team had Tom Smith and John Kirwan who provided many of the crosses for the prolific goalscorer Sandy Brown. The 1921 team had 20-year-old Jimmy Dimmock who scored the only goal in the Final and made over 400 appearances for the club.

There are many wingers who have been omitted – Terry Medwin, Jimmy Neighbour, Peter Taylor and Ruel Fox and players who played wide in midfield but were really central midfield players or strikers playing a deeper role. After much agonising, here is your list of

14 Tottenham Wingers/Wide Midfield Players For Your Consideration

Sonny Walters

He came through the Tottenham youth system and made his debut during the War. He became a regular in the team from 1949 and was a member of the ‘Push and Run’ team which won the 2nd and 1st Division titles in successive seasons. Playing on the right, he was a speedy, direct winger who had a fierce shot and scored regularly. He played until 1956 and made over 280 appearances for Spurs, scoring 85 goals.

Les Medley

The left winger in the ‘Push and Run’ team, Medley also came through the Tottenham ranks and retained his position from 1949 through to 1953. He also brought pace and trickery to the team and scored 65 goals in 0ver 220 appearances.

George Robb

Played for Spurs throughout the 1950s and was the replacement for Medley. A left winger, he was two footed and was direct and fast with a good shot. He started as an amateur preferring to continue as a school teacher but on Medley’s departure was persuaded to turn professional. He made 200 appearances, scoring 58 goals.

Cliff Jones

A vital member of the Double team he was a regular from 1958 on signing from Swansea through to 1968. A very fast and direct winger who could also jump to great heights to head many important goals. A very brave player who gave everything for the team and was still scoring regularly in his final months with Spurs before his transfer to Fulham. A Welsh international, Jones could play on either wing and also scored 159 goals putting him 4th on the Tottenham all-time goalscoring list.

Cliff Jones and Terry Dyson with the Double team [Photo: Logan Holmes]

Terry Dyson

Dyson was an unsung hero of the Double team. Having made his debut in 1955, he only became a regular in the team in August, 1960 but played a major role in Spurs success. He made 47 appearances on the left and scored 17 goals in the ‘Double’ season  but missed out on the 1962 FA Cup win. He returned for the European Cup Winners’ Cup triumph the following season where he scored twice in the Final against Atletico Madrid. Another player to come through the Spurs ranks, he holds the distinguished record of being the only Spurs player to score a hat-trick against Arsenal.

Jimmy Robertson

Robertson was signed as Bill Nicholson tried to build a new team to replace the ‘Double’ side. It was an unenviable task but Robertson helped Spurs to the 1967 FA Cup success, scoring a goal in both the semi-final and the Final. He was a Scottish international but he fell out of favour when that team failed to make the progress that Nicholson had expected. He is one of only two players to score for both teams in the north London derby. The other is ….?

Ossie Ardiles

As the role changed, players like Ardiles played on the right of midfield. He wasn’t a winger but fulfilled the role on the right of a four or five man midfield. An amazingly skilful player who worked industriously alongside Glenn Hoddle, he will always be remembered by Tottenham fans as a vital member of the team from the 1980s which won two FA Cups and the UEFA Cup.

Tony Galvin

Galvin was another vital member of the 1980s team. A product of non-League football, Galvin was signed from Goole Town. He played on the left, bringing non-stop running from deep positions to the team. He also had the ability to beat a man and deliver accurate crosses. He made over 260 appearances for Spurs and scored 31 goals as Spurs won successive FA Cups in the early ’80s and brought the 1984 UEFA Cup to White Hart Lane.

Chris Waddle

He was signed from Newcastle in July, 1985 for a fee of £590,000 and made an immediate impression by scoring twice on his debut against Watford on the opening day of the season. He made 138 League appearances and scored 33 goals. He was part of the exciting team that David Pleat managed to 3rd in the League and to the FA Cup Final and was a vital part of the 5-man midfield which supplied Clive Allen. His move to Marseilles in France denied Spurs fans the opportunity of seeing the three England internationals, Waddle, Gascoigne and Lineker, playing in the white of Tottenham.

Paul Allen

Signed from West Ham United also scored on his debut against Watford in August, 1985. He played in the 1991 FA Cup winning team on the right side of midfield. He was also part of the 1986-87 midfield quintet who created goalscoring opportunities for his cousin, Clive. A hard-working player, in eight seasons at White Hart Lane he made over 350 appearances and scored 28 goals.

Darren Anderton

Signed in 1992 from Portsmouth, Anderton spent 12 years with the club. He made over 300 appearances for Spurs and scored 44 goals but it would have been many more but for frequent periods out with injury. A member of the 1999 League Cup winning team, at his best when free from injury, he was one of the best to play for Spurs.

David Ginola

At a difficult time for Spurs, Ginola brought artistry, flair and goals to Tottenham. Loved by all, he helped Spurs win the 1999 League Cup and scored many memorable goals. He was the double Footballer of the Year in 1999 and although his time with Spurs was brief he will always be remembered.

Aaron Lennon [Photo: Jav The_DoC_66]

Aaron Lennon

Lennon arrived from Leeds United in 2005 and immediately made an impact on the team. He has been a regular on the right of midfield since then and has shown improvement season by season. He works hard for the team, covering in defence and also creatively with pace on the wing and has the ability to score vital goals.

Gareth Bale

A phenomenal success in the past year, just raising the bar higher with each season. After a difficult time at Spurs in his early years he has become the star around whom Andre Villas-Boas is looking to build his team. Pace, strong running, powerful shooting from all angles and distances, amazing free-kicks, incredible goals – he brings them all and more to the team. Not surprisingly, he is the target for every top club but Tottenham are determined to hold on to their prize asset.

My Team Selection:

An incredibly talented collection of wingers and I know I’ll upset many by omitting David Ginola from my selection but I have chosen the two Welsh wingers, Cliff Jones, a true Tottenham ‘Legend’ to play on the right with his young compatriot Gareth Bale on the left.

Your Choice?

From the wide midfield players listed, please select the best two who you have seen playing. If there is anyone you think should have been on the list, please add his name in the comments at the end of the page and also let me know your views on Tottenham’s wingers over the years.

Vote on HotspurHQ’s Team Selection Poll: (Select 2)


Tags: Cliff Jones Soccer Tottenham Hotspur Wide Midfield Wingers

  • Gareth Rogers

    Although undoubtedly a great world-class player, with Bale at the top all it proves is that most people who have voted are younger. He is going to be one of the best wingers in the world but one great season does not make a great player, and especially at Bale’s age. He still has a lot to prove to be considered one of the best ever, and with names like Ginola, Waddle and Ardiles having played at the club and even Darren Anderton, who in my opinion, would have played more for England than Beckham if he had not of been injured so much. It is most definitely my hope that he does become our best ever and that he helps take us to the Champion’s League next season and to genuine title contenders over the coming years, but to call him the best ever yet is just too soon.

    • Logan Holmes

      It was obvious that Bale would be first choice for many given the past few seasons he’s had. Hopefully, he will carry that form into next season so that the team as a whole can develop into a Champions League side with the prospect of winning trophies.

      Compared to what Cliff Jones achieved in his time with Spurs, Bale has a long way to go but it’s great to be able to have this type of discussion on current players comparing them favourably with past Tottenham Legends.

      • Gareth Rogers

        I agree with all of what you say Logan. It just grinds my gears when people forget about the legends that built the club into what it is today. Without the likes of Cliff Jones, Jimmy Greaves, Hoddle, Waddle and the likes Gareth Bale would be playing at a completely different club right now it’s these legends that have built the club to be where it is today and make great players like Paulinho want to come to the club. We have a great history and although I’m not the sort of person who is stuck in the past I just think a club like ours is built on that history and to pick Bale as the best winger ever at the club doesn’t do justice to all the great history that today’s success and the success gong forward is built on.

        • Logan Holmes

          I know what you mean and totally agree with you. That’s why I regularly include articles on the blog which cover some of Tottenham’s history.

          It’s like the re-writing of football history – everything is now thought of as in the Premier League era as if football hadn’t existed before 1992. When stats are being used for top goalscorers etc it’s in the PL, totally overlooking what happened before then.

          Spurs have a great history and one to be remembered, celebrated and built on.

  • the daily hots

    best ever is David Ginola he played for the team not himself his skill was amazing to watch ok bales had a good couple of seasons but ginola did it for a few more and never moaned about anything not like the players of today who are not loyal to the club

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