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17. George Hunt
During his seven seasons with Tottenham in the 1930s, Hunt scored 138 goals in 198 games and helped them win promotion to the First Division 1932/33. He’s still sixth on the all-time scorers list at White Hart Lane, and would be higher if his goal-grabbing feats hadn’t attracted the attention of Arsenal, who snapped him up for £7,500 as a replacement for the injured Ted Drake.
The Gunners won the league in his only season with them, but Hunt’s three-goal contribution was minimal and he left for Bolton when Drake returned.
16. Rohan Ricketts
The 34-year-old has quite the CV, but it all started with Arsenal, where he was part of the side which won the FA Youth Cup in 2000 and 2001. Ricketts found it hard to break into the first team, though, and made just one appearance in the League Cup before switching to Spurs.
He broke into Tottenham team in 2003/04, making 28 appearances and scoring two goals. But that was the peak of his career: since leaving Spurs in 2005, it’s been a long slow slide down the divisions via Canada, Hungary, Moldova, Bangladesh and numerous other footballing backwaters.
15. Clive Allen
A man with more London destinations than the Tube – he’s also played for QPR, Palace, Chelsea, West Ham and Millwall – Allen never kicked a competitive ball for Arsenal: signed in summer 1980 from the Rs, he was promptly swapped for Palace left-back Kenny Sansom. (He had just about enough time there to be pictured above, at left with Terry Neill and John Hollins.)
By contrast, Spurs was the longest stay and biggest success of a peripatetic career, which peaked with his 1986/87 season: 49 goals, an a FA Cup final and both the Players’ and Writers’ Player of the Year.
14. Willie Young
Imposing centre-back ‘Big Willie’ joined Tottenham from Aberdeen under manager Terry Neill in 1975, making 63 appearances in two seasons – including a north London derby in which he was sent off for what The Scotsman called a “kung-fu assault”.
When Neill made the move across north London, he brought Young with him. The Scot immediately became a first-team regular and duly won favour with the Arsenal fans, who unveiled the rousing chant, “We’ve got the biggest Willie in the land”. In the 1970s, you made your own fun.
Young made more than 170 appearances for the Gunners, and reached three FA Cup finals and the Cup Winners’ Cup final in his four seasons at the club.
13. Freddie Cox
War gets in the way: Reading-born winger Cox had just broken into Tottenham’s first team when he had to switch for a different wing, as an RAF fighter pilot who won the Distinguished Flying Cross. Demobbed, he played three post-war seasons for Spurs before a £12,000 switch to Arsenal in September 1949.
He can lay a fair claim to have won the 1950 FA Cup for them – he scored in the semi against Chelsea, then the winner in the replay, then set up the winner in the final against Liverpool. Two years later he was t it again, bagging two in the Cup semi against a presumably fuming Chelsea, but Arsenal lost at Wembley to Newcastle.
12. David Bentley
Bentley had joined the Gunners as a 13-year-old but struggled to break into what was then a stellar squad. His involvement was limited to cup competitions and a solitary league appearance against Portsmouth towards the end of the Invincibles season.
Bentley then had loan spells at Norwich and Blackburn Rovers, signing full-time for the latter in 2006. Two years later, he joined Spurs for £15m, but he soon slipped down the pecking order at White Hart Lane and was sent on loan to four different clubs.
The winger’s most notable contribution in a Spurs shirt was a dipping 43-yard-volley in a memorable 4-4 draw against Arsenal at the Emirates.
11. David Jenkins
Signing pro terms with Arsenal at 17, Bristolian winger Jenkins (pictured above right with a young Bob Wilson) had to wait four years for a debut and was then gone within 11 months. In that time he managed three goals, 17 top-flight games and a start in the 1968 League Cup Final (they lost to Leeds and he was substituted for Terry Neill).
10. Jimmy Robertson
The Flying Scotsman was a fan favourite at Tottenham, particularly for his goal against Chelsea in the 1967 FA Cup Final. In six seasons at Spurs, the tricky winger scored 33 goals in 182 games, before joining Arsenal in a surprising straight swap for David Jenkins that left Spurs fans feeling hard done by.
Robertson only spent 18 months with the Gunners, playing 59 times and scoring eight, before joining Bobby Robson’s Ipswich.
9. William Gallas
Gallas joined Arsenal from Chelsea, where he’d allegedly threatened to score own goals if he wasn’t allowed to leave, and carried that calm demeanour into his Gunners career. In 2007 he was surprisingly named as club captain, but things started to unravel when he criticised the squad in an interview.
After his contract expired (it supposedly wasn’t renewed due to “unreasonable demands”) the defender joined Tottenham on a free, with Spurs boss Harry Redknapp describing the move as a “no-brainer”. The Lilywhites reached the Champions League quarter-finals in Gallas’ first season, but injuries plagued his final two years at the club.
8. Laurie Brown
A Geordie who started as an amateur and represented Great Britain at the 1960 Olympics, Brown turned professional with Northampton and his goals earned him a move to Arsenal. They converted him to a centre-half but only used him sporadically – then controversially sold him to Spurs on the eve of a north London Derby.
7. Steve Walford
Highgate-born centre-half who started his career at Spurs in 1974. He barely figured for the Lilywhites but had shown enough for former Spurs boss Terry Neill to take him across north London for £25,000 in 1977. He got more game-time in red, featuring in nearly 100 matches including the last seven minutes of the 1979 FA Cup Final against Manchester United: Arsenal promptly discarded a two-goal lead, only for Alan Sunderland to bag a late winner. He’s pictured above at back left, somewhat sheepishly joining in the celebrations.
Walford left in 1980 and, bearing an increasing resemblance to Ronnie Barker’s Porridge character Fletch, went on to become Martin O’Neill’s sidekick at Wycombe, Norwich, Leicester, Celtic, Villa, Sunderland and the Republic of Ireland.
5. Jimmy Brain
The striker kicked off his Arsenal career with a debut goal in the north London derby - and Brain didn’t look back from there. He was the top scorer for four seasons in a row, including 39 strikes in the 1925/26 season; in total, he bagged 139 goals in 232 appearances for the Gunners and is still joint fifth on the all-time scorers list, level with Ted Drake.
4. Terry Neill
Perhaps a slight rule-bend here as he didn’t actually play for both sides, but he did manage both – via a controversial direct switch. Having played 272 times playing for Arsenal and become the club’s youngest-ever captain at 20, the Ulsterman became Hull’s player-manager at 28 then switched to Tottenham in 1974.
In the hot summer of 1976 he flitted across the great divide and proceeded to lead Arsenal to three successive FA Cup finals (winning one) and the 1980 UEFA Cup Final. He’s pictured above at left, toasting future divide-hopper Pat Jennings.
3. Emmanuel Adebayor
The striker has performed the impressive feat of alienating fans on both sides of the north London divide. Adebayor joined the Gunners in 2006 and flourished after Thierry Henry’s departure, netting a healthy 62 goals in 142 appearances before being swept up in Manchester City’s nouveau riche shopping spree.
2. Harry Kane
Spurs followers may laud him as one of their own, but Kane’s first dalliance with a Premier League club was in the red of Arsenal when he was just eight years old.
He was released after just one season with the club, though, and eventually joined Tottenham at the age of 11. Just imagine what might have been, Gunners fans…
1. Sol Campbell
The defender spent nine happy seasons at White Hart Lane, before breaking Spurs supporters’ hearts by joining their bitter rivals for free.
The move made Campbell persona non grata at White Hart Lane, but he later sealed the Premier League title with Arsenal at the home of the Gunners’ adversaries. That was one of four major trophies the defender won under Arsene Wenger; although his time at Tottenham yielded just a single League Cup, Campbell was largely excellent at both clubs.
