15 Greatest Tottenham Wingers
Of the considerable talents to have played for Tottenham Hotspur over the years, some of the finest have been found on the wings.
Naturally, there have been varieties in how these wingers have been deployed, but essentially their objectives have remained the same: get up and down the flanks, help your full-back, beat your man and provide service in the final third.
Fortunately for Tottenham supporters, those charged with these tasks have proved a lot more entertaining than those descriptions.
The following list attempts to rank the 15 greatest wingers to have played for the North London club.
Many of those featured could cite more expansive roles than that of wide-men. It is skipping purposely, often eye-catchingly in reach of the touchlines, though, where their respective talents are primarily associated.
Only post-World War Two candidates have been included. Properly assessing players pre-1960 is challenging enough, but with a lot less living and/or recent testimony to their talent than their more contemporary counterparts, those even further back are sadly harder to compare with.
Criteria for inclusion and ranking is based on a mix of individual ability—what the players offered as wingers and their contributions to the greater Tottenham cause.
Essentially though, it comes down to this writer's opinion through the interpretation of these factors.
Regardless of your opinion about the list, it will hopefully at least provide an excuse to celebrate Spurs' best ever wingers.
15. Jimmy Neighbour and 14. Jimmy Pearce
Beginning our list of Tottenham's 15 greatest wingers are a pair from the 1970s, a time when the club's main talent was largely to be found in more central positions.
Jimmy Pearce was a utility player deployed in varying roles who found himself most comfortable on the wing.
His career was halted prematurely in 1973 due to a rare bone condition, but by that point he had played in almost 200 games for Spurs, scoring 35 times in the process.
Pearce's finishing was well regarded, and he scored in his team's runs to 1971 and 1973 League Cup victories (though he only played in the latter final) as well as the UEFA Cup in between.
The ability to perform as a convincing striker extended to his comfort cutting-in from his position on the flanks—an attribute aided by his considerable skill and understanding of the arts of deception in beating a man.
Jimmy Neighbour followed his namesake, playing 156 times in all and similarly (though for a different reason) struggling to hold down a regular place in the team.
Neighbour was not quite the match talent-wise of some of Spurs' stronger players of the time, but he was a convincing winger all the same.
Mazy runs, pinpoint crosses and a willingness to put a shift in were among his chief attributes. Neighbour enjoyed his best time individually at Tottenham during their mid-70s decline, but ultimately, the arriving manager Keith Burkinshaw decided to look elsewhere.
13. George Robb and 12. Jimmy Robertson
George Robb and Jimmy Robertson both shared narrowly missing out on Tottenham's title successes of their respective decades. More positively though, they can both claim to be two of the more exciting players of the eras that followed.
Also a teacher by trade, Robb replaced Les Medley of Arthur Rowe's title-winning side of 1950-51 and established himself on the left wing well into Bill Nicholson's tenure.
While he will go down in greater football folklore as a member of the England team that was taught a footballing-lesson by Hungary in 1953 (his only England cap), for Spurs, he was a consistent and valuable performer. Combining an aggressive style with solid service for his forwards, Robb left White Hart Lane in 1958 having scored 58 goals of his own.
Robertson's Wembley experience was a more pleasant one than Robb's—the Scotsman scored the opener in Spurs' 2-1 defeat of Chelsea in the 1967 FA Cup final.
At his best in full flow, his quickness left opponents in his wake given the space to charge into. Generally found out right, his subsequent crossing and passing was at its best in these moments rather than in more stationary positions.
Swapped with Arsenal's David Jenkins in 1968, Spurs supporters felt they lost out in the departure of their young winger, Robertson.
11. Tony Galvin and 10. Ralph Coates
Tony Galvin and Ralph Coates were two players who embodied the workmanlike values that typify some wingers—honesty in application, hard-running and all-round graft.
Yet while these were the attributes most commonly associated with their respective times at Tottenham (and there is certainly nothing wrong with that), they sometimes serve to undervalue the quality of their involvement.
Coates was a star at Burnley. That status was never likely to be matched in a Spurs side with international talents such as Martin Chivers, Alan Mullery and Martin Peters.
Still, he proved himself a valuable part of Bill Nicholson's strong squad of the early 1970s. He had the winger's craft to beat a man and beyond that, could do something with the ball (later, he also featured centrally).
Most notable here was his winner off the bench in the 1973 League Cup Final over Norwich City (as seen in the video above).
Galvin would not enjoy such an immediately identifiable moment but can claim his part in the successes of the early 1980s.
The left winger's persistence and stamina provided a steady outlet in midfield, one that balanced the more creative leanings of others such as Ossie Ardiles and Glenn Hoddle.
Appearing in each of Spurs' victorious cup finals, here was a player that manager Keith Burkinshaw could most definitely rely on.
9. Gareth Bale
Gareth Bale embodies the debate that so often goes with compiling lists such as these.
Ability-wise, the Welshman compares with anyone on it. Even with his central sojourns, particularly during last season, his contributions on the wing have been plentiful and dazzling.
Ultimately though, a decision to value the greater longevity and/or success of others at Tottenham was chosen in deciding his ranking (and that was considering Champions League qualifications as modern equivalents to cups).
Nonetheless, from the moment he was properly pushed forward into left midfield late in the 2009-10 campaign, Bale has been a joy to watch.
The scintillating, rapid sideline runs such as those that terrorised Internazionale in 2010;the goals that both demonstrated his instincts cutting inside (Arsenal and Chelsea that same year spring to mind);and his spectacular shooting ability (take your pick from last season)—there was plenty of evidence that convinced Real Madrid to spend 100 million euros on him this past summer.
Perhaps another year or two at Spurs would have upped Bale's standing among the club's greatest wingers in this writer's mind. Some of you might believe his ability warrants that recognition anyway.
Here he is, though, a definite part of the conversation, just not one of its concluding names.
8. Aaron Lennon
Longevity gives Aaron Lennon the edge over Bale on this list. You could argue the other way around on talent and productivity, but the role Lennon has played in engineering Tottenham's current era of competitiveness should not be underestimated.
Lennon joined Spurs in the summer of 2005, as did another pacy winger in Wayne Routledge. The latter was more experienced at that point, but an injury early in the season saw his younger teammate get a chance.
The sheer speed the small midfielder possessed—and his ability to utilise it with impressive control—was frightening.
His arrival was part of genuine improvements in the overall talent level at Spurs. Possessing plenty of guile (Robbie Keane), craft (Michael Carrick) and defensive steel (Edgar Davids, Ledley King), Lennon injected the pace that gave the team another level.
Injuries have stopped Lennon playing as often as would have been liked (2012-13 was the first time he played over 40 games for Spurs), but not a season has gone by when he has not been an important cog in the machine.
He tormented many a full-back with direct running and thrilling last-ditch changes in direction—28 goals and 64 assists in eight seasons is no bad return for a player with supposedly no end-product.
Even if more tangible contributions in front of goal might have been nice, just the menace of Lennon is something Spurs have seldom been able to do without.
7. Les Medley and 6. Sonny Walters
These entries may be a concession to the history books, but Tottenham's past is so important to its present that to not include an entry from their first top-flight title winning side would be a questionable oversight.
Difficult as it might be to judge Sonny Walters and Les Medley compared to others on this list, their contributions to Arthur Rowe's "push and run" side make them more than worthy of their placings.
Left winger Medley joined prior to his right-sided counterpart Walters but would not ultimately last as long as Walters.
Medley's goal tally went into double figures in both the Division Two and Division One title successes of 1949-50 and 1950-51.
He was a sturdy figure who could handle himself aerially and was particularly handy combining in quick give-and-goes with teammates on the left.
Walters was similarly inclined, possessing the insight and work ethic to get involved in deeper positions, as well as further-forward.
The latter was marked by his explosiveness off the mark, though his 71 goals in almost a decade were good for his efforts, too.
5. Terry Medwin and 4. Terry Dyson
In the 2008 edition of the Tottenham Hotspur Player by Player guide, coauthor Ivan Ponting describes Terry Dyson—a member of the great side of the early 1960s—as "a hyperactive beaver who could contribute in all areas of the pitch and who would donate his dying breath to the common cause." Ponting further adds:
Admittedly the Dyson distribution was wild at times, and he was not always quick to spot the most profitable passing option, but he compensated amply by perpetual motion and bravery, and his finishing, too, could be lethal.
Forgive the sizable referencing from the aforementioned guide, but Ponting's description of Dyson struck a chord. Skill, quickness and flawless deliveries are so frequently demanded of the modern wide-man. Here was a reminder that there is more to play on the flanks.
Though his work ethic was his most recognisable trait, Dyson was no slouch. The star of Spurs' European Cup Winners' Cup final 5-1 thrashing of Atletico Madrid in 1963 (see above video) was quick in his own right and, as Ponting describes, a constant menace.
Operating on left, Dyson was an ideal counterpoint to Cliff Jones in Bill Nicholson's team back then.
Fortunately for the soon-to-become legendary manager, he had another in the form of Jones' compatriot Terry Medwin.
The Wales international preferred to play on the right wing and was an even better scorer than Dyson (notching 73 overall compared to Dyson's still-admirable 55).
The similarly dangerous Medwin earned a league winner's medal in the Double season, having deputised enough for his fellow wingers.
Regarded as a more talented footballer than Dyson, a slight deficit in grit saw him as the understudy that year. Still, before and afterwards he remained a vital part of the squad, and played in the 1962 FA Cup final win over Burnley.
3. Chris Waddle
It is one of the great disappointments of Tottenham history that the club's problematic financial situation in the late 1980s denied them the coming together of three of English football's best talents of the time.
Just as they signed Gary Lineker from Barcelona in the summer of 1989, Chris Waddle departed for the continent as he was sold to Marseille. Along with Paul Gascoigne—who worked so well with both—that trio might have launched an era in North London as good as that which had started the decade.
Alas, football is made up of such "what if?" questions. Spurs fans were fortunate to get the four years of Waddle they received.
The 1985 signing from Newcastle took a little time in settling, but once he had, the mesmeric dribbling and turns that were his trademark soon lit up White Hart Lane.
Bamboozling opponents out-wide before searching threateningly inwards, Waddle was as fine an exponent in the art of wing-play as English football has ever seen.
At Spurs, he was one of the nearly-men of David Pleat's so-close yet so-far side of 1986-87, the young buck in a midfield that also featured the veteran stars Ossie Ardiles and Glenn Hoddle.
His final season is regarded as his finest individually in N17 and one that offered a tantalising glimpse of what might have followed alongside Gascoigne.
2. David Ginola
Ahead of some more successful Lilywhites, David Ginola is, nonetheless, extremely deserving of this lofty position.
The swashbuckling, charismatic Frenchman was a remarkable talent who invigorated Tottenham across the width of the pitch. Be it through his exemplary crossing, thrilling runs inside or spectacular shooting, he was the star who inspired Spurs' best moments around the turn of the millennium.
One of those was the run to the club's 1999 League Cup success. Achievement-wise, it might not compare to those of the teams Dyson or Walters were part of, but in the context of the modern era, it was a rare triumph for Spurs.
Ginola was a rare player for the North Londoners in those relatively lean years. There was talent beside him, but he was the main man for whom other fans might watch with envy.
More than just an entertainer, he played a leading role in helping Spurs avoid relegation in 1997-98 and was an undoubted catalyst for the improvement that helped land the League Cup a year later (for which he was awarded the FWA and PFA player of the year awards).
Accusations of laziness were misguided—even from a comparatively peripheral position, he consistently found ways to influence.
1. Cliff Jones
On a list of Tottenham's 20 Best Players of All Time from earlier this year, this writer ranked Cliff Jones at no. 7.
Given that made him the highest-ranked winger on there, it would have been strange six months later to choose anyone different on this list.
Jones is wholly deserving of recognition as Spurs' greatest winger.
Recently inducted into the National Football Hall of Fame, the Welshman was a versatile and highly productive attacking-threat in Bill Nicholson's successful side of the early 1960s.
Danny Blanchflower and Dave Mackay are primarily regarded as the key players of the 1960-61 Double side in particular. Jones, though, was the standout in taking the stylish football philosophy of that team and making it sparkle.
Depending on where Nicholson needed him, he could operate on either side of the pitch. In addition to being quick and extremely skillful at taking opponents on, he was also as daring as they come.
That bravery, coupled with good timing and positional sense, contributed to the 159 goals Jones would score in a Spurs shirt—a remarkable tally for a striker, let alone a winger.
The later years of his 10-year spell were undermined by injury, but even then, he could be relied upon for a moment or two that rolled back the years.
Jones, 78, remains a regular presence at White Hart Lane to this day. His entry into the National Football Hall of Fame is worthy recognition of a class act, on and off the pitch.