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The history of players turning out for both teams goes all the way back to the 1930s. Jimmy Brain was a prolific striker who bagged 139 goals in 232 Arsenal appearances before joining Tottenham in 1931. His record there was less impressive—he scored just 10 times in four years.
In the 1930s, George Hunt and Freddie Cox both moved in the opposite direction from Tottenham to Arsenal. Like Brain, Hunt had a far better record at one club than the other. He struck 137 times for Spurs but managed just three goals in a Gunners shirt. Cox was more consistent, playing around 100 times for each club and generally acquitting himself well.
Vic Groves was a stalwart of Arsenal in the 1950s and 1960s, but he had already made a few appearances for Spurs before joining the Gunners. In the early '60s, he was a team-mate of central defender Laurie Brown, who left Arsenal after three years with the club to join Tottenham.
In 1968, Spurs' Jimmy Robertson and Arsenal's David Jenkins were involved in a swap deal that took them to opposite ends of the Seven Sisters Road. Arguably, neither player repeated the success he had at his initial club.
Steve Walford made just one appearance for Tottenham, but he did mark it with a goal. However, he made a far greater impression at Arsenal, pocketing an FA Cup winner’s medal in 1979. Also with the club at that time was Kevin Stead, who made just 16 appearances in total for the two north London sides.
Rohan Ricketts was a graduate of Arsenal’s youth scheme who made only a solitary appearance at Highbury before joining Tottenham in 2002. After a bright start, he faded into relative obscurity. The same fate ultimately befell David Bentley, who squandered his talent at both clubs either side of a successful spell with Blackburn Rovers.