Tottenham Hotspur’s history is littered with some of the finest professional footballers ever to grace the world’s greatest sport.
Given the club’s lack of success in recent years, it is little wonder that most of the club’s best signings were made during the 20th century.
With that in mind, read on as we look at the best Tottenham transfers of all time, starting with a truly legendary figure from yesteryear.
Dave Mackay
Brian Clough described Dave Mackay as Tottenham’s greatest-ever player, while George Best claimed he was the hardest man he had played against.
Signed from Hearts for £32,000 in March 1959, Mackay was an inspirational leader who played a key role in Spurs’ success during the 1960s.
He won a league title, three FA Cups and a European Cup Winners’ Cup with the club. When he was out with a serious injury, the silverware dried up.
Ossie Ardiles & Ricky Villa
Tottenham’s move for Argentinian internationals Ossie Ardiles and Ricky Villa in 1978 was undoubtedly one of the most surprising transfers in football history.
Players born overseas had traditionally been a novelty in English football, but changes to European law completely changed the landscape.
The pair helped Tottenham win back-to-back FA Cups during the early 1980s. Ardiles also lifted the UEFA Cup with the club in 1983/84.
Pat Jennings
Goalkeeper Pat Jennings made 591 appearances in 13 seasons at Tottenham after signing from Watford for £27,000 in 1964.
He won two League Cups, an FA Cup and a UEFA Cup during his time with the club, before being surprisedly sold to Arsenal in 1977.
Tottenham thought he was approaching the end of his career, but he went on to make another 327 appearances for their local rivals.
Jimmy Greaves
Greaves scored 268 goals in 381 games in nine seasons at Tottenham, and was the club’s all-time leading goalscorer until overtaken by Harry Kane in 2023.
He helped Spurs win two FA Cups and a first ever European trophy for an English club as they beat Atletico Madrid 5-1 in the 1962/63 European Cup Winners’ Cup final.
Despite losing his scoring record to Kane, many fans still believe that Greaves is the greatest striker ever to represent the club.
Bobby Smith
Bobby Smith is also held in high regard by Tottenham supporters after scoring 208 goals in 317 appearances for the club between 1955 and 1964.
They paid £18,000 to sign Smith from Chelsea and the move proved to be inspired as he subsequently helped Tottenham win the league and cup double in 1960/61.
Further successes followed in the FA Cup (1961/62) and European Cup Winners’ Cup (1962/63) before he moved to Brighton & Hove Albion in 1964.
Danny Blanchflower
Danny Blacnhflower joined Tottenham from Aston Villa in 1954 for £30,000 and went on to become the heartbeat of the club’s golden era.
He was twice named Footballer of the Year and ranked by the Times as the greatest player in Tottenham’s history in 2009.
His ability on the ball, eye for a pass and leadership skills set him apart from his peers. In simple terms, Blanchflower is a true Tottenham legend.
Gareth Bale
Gareth Bale arguably deserves two entries on the list of best Tottenham transfers of all time, starting with his £5 million move from Southampton in 2007.
He subsequently enjoyed a glittering spell with the club before completing a stunning £85.1m switch to Spanish giants Real Madrid in 2013.
Spurs ultimately wasted the profit they made on Bale, bringing in players who largely failed to live up to expectations. Christian Eriksen was the exception.