The 10 best Tottenham players of all time

We pick out the greatest footballers to have pulled on a Spurs shirt over the years.

10. Paul Gascoigne

After playing 104 times for Newcastle United, Gascoigne moved south to Tottenham for a British record fee of £2.2m in 1988. He was a qualified success in his first season at the club but only got better as time went on, winning Spurs’ Player of the Year award in 1989/90 and starring in Terry Venables’ side’s run to the FA Cup final the following campaign.

Gascoigne’s free-kick against Arsenal in that season’s semi-final remains one of Tottenham’s most famous goals, although the midfielder was never really the same again after sustaining a serious cruciate ligament injury in the Wembley showpiece against Nottingham Forest.

9. Ossie Ardiles

Every top-tier club is packed with foreign players these days, but it was not always so common for English sides to employ overseas footballers. Indeed, there was considerable intrigue when Argentinian duo Ardiles and Ricky Villa pitched up at White Hart Lane shortly after the 1978 World Cup, which had been held in the pair’s homeland.

Ardiles was a key part of Spurs’ triumphs in the FA Cup in 1981 and the UEFA Cup three years later, and spent a decade at the club in total (although after the outbreak of the Falklands War, the midfielder spent much of the 1982/83 campaign at Paris Saint-Germain).

8. Pat Jennings

The finest goalkeeper to ever play for Tottenham, Jennings spent 13 years at White Hart Lane between 1964 and 1977. The Northern Ireland international pulled on a Spurs shirt 673 times and won two League Cups, an FA Cup and a UEFA Cup under the guidance of legendary boss Bill Nicholson.

He was also named FWA Footballer of the Year in 1973 and PFA Player of the Year in 1976 – prizes which have been won by just two other goalkeepers since.

7. Bobby Smith

Smith is one of just two men to have broken the 200-goal barrier for Tottenham, with his 208 strikes for the north London outfit placing him behind only Jimmy Greaves in the all-time rankings. He was an integral part of the team which won the double in 1960/61, as Spurs became the first side to claim both the First Division title and the FA Cup in the same season since Aston Villa in 1896/97.

Smith scored in the final of the FA Cup in both 1961 and 1962, while he helped Tottenham win their first ever European trophy – the Cup Winners’ Cup – in 1963.

6. Steve Perryman

No player has made more appearances for Spurs than Perryman, who turned out in a total of 854 games for the capital club. The longevity of the defender, who began his career further forward in midfield, was rewarded with six major honours: a pair of FA Cups in 1981 and 1982, two League Cups in 1971 and 1973, and two UEFA Cups in 1972 and 1984.

Perryman won the FWA Footballer of the Year prize in 1982, when he appeared in all 65 of Spurs’ games across four different competitions, as well as the Charity Shield defeat by Liverpool.

5. Martin Chivers

Only two men have scored more goals for Tottenham than Chivers, who made the net ripple 202 times in his 415 appearances for the Spurs first team. The striker actually took a while to break into the side as Jimmy Greaves and Alan Gilzean continued to be paired up top, but by the start of the 1970s he was a key player for Bill Nicholson’s charges.

Chivers won a couple of League Cups and the UEFA Cup during his eight years at the club, with the 1971/72 season – when he scored 44 goals in all competitions – his best in a Tottenham shirt.

4. Glenn Hoddle

One of the most naturally talented footballers the English game has ever produced, Hoddle played almost 500 games for Spurs – who he first joined as an apprentice at the age of 12 – between 1975 and 1987.

The midfielder won two FA Cups and a UEFA Cup at White Hart Lane (although he was absent from the latter final due to injury), with his range of passing and all-round technical quality frequently wowing Tottenham fans. 

3. Jimmy Greaves

Bill Nicholson, wary of the likely pressure Greaves would automatically be under if he became the first £100,000 player in British football, paid £99,000 for the centre-forward’s signature at the end of 1961.

That meant he missed Spurs’ greatest ever season – the First Division and FA Cup double – by a matter of months, but Greaves did go on to win two FA Cups and the Cup Winners’ Cup at White Hart Lane. He remains Tottenham’s highest scorer of all time with 266 goals, a tally which includes 222 in the top flight.

2. Dave MacKay

MacKay had helped Hearts claim three pieces of silverware in the 1950s, which persuaded Spurs to bring the Scot south to England at the end of the decade.

The left-half immediately became an important member of Bill Nicholson’s squad and was one of the key figures in the most trophy-laden period in Tottenham’s history: as well as the 1960/61 double, the fiercely competitive MacKay helped Spurs to three FA Cups and the Cup Winners’ Cup, before departing for Derby County – where he won another league crown – in 1968.

1. Danny Blanchflower

The captain of the famous double-winning side, Blanchflower is widely regarded as Tottenham’s greatest ever player. The Northern Irish right-half made 382 appearances for the club, winning the First Division, two FA Cups and the Cup Winners’ Cup between 1954 and 1964, a decade in which he was twice named FWA Footballer of the Year.

“The game is about glory, it is about doing things in style and with a flourish, about going out and beating the other lot, not waiting for them to die of boredom,” Blanchflower once said. It summed his mindset up perfectly.

By Greg Lea

Greg Lea is a freelance football writer for FourFourTwo, The Blizzard and various others. Follow his Twitter account @GregLeaFootball for anything and everything related to soccer and more.