The North London rivalry has produced some of English football's fiercest moments, making any direct move between Tottenham Hotspur and Arsenal one of the rarest and most controversial transfers in the game. That exclusive list has now grown once again following the arrival of teenage defender Elijah Upson.
Fabrizio Romano had reported that the agreement had been signed for the 18-year-old centre-back to join Arsenal's long-term project. Romano also revealed that Upson rejected a new contract offer from Tottenham in order to make the switch across North London, with the move expected to be officially announced shortly.
With Upson becoming the latest player to cross one of football's biggest divides, here is the updated list of every player to move directly from Spurs to Arsenal.
George Hunt
George Hunt was one of the earliest footballers to make the controversial switch from Tottenham to Arsenal. The prolific striker moved to the Gunners in 1937 after establishing himself as a reliable goalscorer at Spurs. During his time at Arsenal, Hunt enjoyed significant success, helping the club continue its dominance under legendary manager Herbert Chapman and his successors.
Freddie Cox
Freddie Cox made the move from Tottenham to Arsenal in the 1949. The Welsh winger was known for his consistency and reliability, becoming a dependable figure for Arsenal at the time. Although transfers between the two clubs were uncommon even then, Cox adapted well and enjoyed several productive seasons in North London with the Gunners.
Vic Groves
Vic Groves crossed the divide in 1955 after playing his early professional career at Tottenham. The versatile winger developed into a dependable first-team player for Arsenal, making near to 200 appearances for the club. His longevity and versatility ensured he became one of Arsenal's most trusted players throughout the late 1950s and early 1960s.
Steve Walford
Steve Walford joined Arsenal from Tottenham in 1977 after struggling to establish himself in Spurs' senior side. The defender proved to be a valuable acquisition for the Gunners, making more than 90 appearances across all competitions. Walford's consistency and commitment made him a fan favourite during his lengthy stay at Highbury.
Willie Young
Scottish centre-back Willie Young swapped Tottenham for Arsenal in 1977. Renowned for his physical style and commanding aerial presence, Young quickly became an important figure in Arsenal's defence. He famously played in three consecutive FA Cup finals between 1978 and 1980, helping the club lift the trophy in 1979.
Pat Jennings
Perhaps one of the greatest goalkeepers in British football history, Pat Jennings made one of the most shocking transfers ever seen between the two rivals. After more than a decade at Tottenham, Jennings joined Arsenal in 1977 and continued performing at an elite level. He made over 300 appearances for the Gunners and remains one of the few players universally respected by supporters of both clubs.
Sol Campbell
No list is complete without Sol Campbell, whose move in 2001 remains arguably the most controversial transfer in Premier League history. Having captained Tottenham and publicly suggested he would stay, Campbell instead joined Arsenal on a free transfer after his contract expired.
The England international became a cornerstone of Arsène Wenger's defence, winning two Premier League titles, three FA Cups and famously playing every league match during Arsenal's unbeaten "Invincibles" season in 2003-04. For many supporters, Campbell's transfer remains the defining example of a player crossing the North London divide.
Elijah Upson (Latest Addition)
Elijah Upson is now the newest name on this exclusive list. The highly-rated 18-year-old centre-back spent 11 years in Tottenham's academy before deciding his future lay across North London with Arsenal. By rejecting Spurs' contract offer and committing to Arsenal's long-term project, Upson has become the latest youngster to make one of English football's boldest career moves.
While he is yet to make a senior appearance, Arsenal clearly believe the England youth international possesses the potential to become an important first-team player in the years ahead.
Final Thoughts
Direct transfers between Tottenham Hotspur and Arsenal remain exceptionally rare because of the fierce rivalry between the two clubs. From George Hunt's historic switch to Sol Campbell's unforgettable free transfer and now Elijah Upson's move, each transfer has attracted enormous attention. Whether Upson can follow in the footsteps of some of the successful names on this exclusive list will be one of the intriguing stories to watch as his Arsenal journey begins.
