Paul Stewart who scored a goal for Spurs in the 1991 FA Cup Final signed from Manchester City as a striker but became a very useful midfield player at White Hart Lane, going on to play three games for England. Bert Sproston is one of the more unusual transfers between the two clubs in the season leading up to the Second World War. Emmanuel Adebayor joined City from Arsenal in 2009 after three years in North London but spent the second half the 2010-11 season on loan at Real Madrid where he scored twice as the Spanish club knock Spurs out of the Champions League. These added to his eight goals in nine north London derbies. He failed to score for City in three games against Spurs and redeemed himself somewhat, in the eyes of Spurs supporters, by scoring on his Spurs debut against Wolverhampton Wanderers and twice on his home debut against Liverpool. The successful season on loan has been followed by a disappointing 16 months following his permanent move to Spurs.
Emmanuel Adebayor’s loan transfer from Manchester City to Tottenham in August, 2011 and his permanent move a year later is the latest player to join Spurs have from City. Vedran Corluka moved south in September, 2008 and Paul Stewart moved from Maine Road to White Hart Lane in 1988. The last player to move in the opposite direction was Chris Jones who joined City in September, 1982.
Vedran Corluka joined Tottenham in the summer of 2008 from City and played mostly at right back although did occasionally play in central defence. He linked well on the right with Aaron Lennon and was one of four Croatians that were at White Hart lane at a time. The arrival of Kyle Walker in the team, limited his opportunities and he left on loan to Bayer Leverkusen and then in a permanent move to Lokomotiv Moscow in the summer of 2012.
Paul Stewart started his career with Blackpool, and joined Manchester City in March, 1987. He scored 26 League goals for City and fifteen months later joined Spurs for £1.7 million. Stewart made his debut for Spurs on 1st October 1988, as a substitute in a 2-2 draw at home to Manchester United but missed a penalty. Bought as a striker he scored 12 goals in his first League season with Spurs but when his goals dried up, he was successfully converted to a midfield role. He was part of the Tottenham midfield which won the FA Cup in 1991, scoring Spurs’ equalizing goal in that game. His conversion to midfield came about almost by accident as Spurs, already a goal down, had to adjust when they were reduced to nine men against Luton Town and Stewart moved back into midfield where he showed an unexpected talent in the position, scoring both goals as Spurs won 2 – 1. In the summer of 1992 he moved to Liverpool, having expressed the desire to return north but it was an unsuccessful period at Anfield. He made 131 League appearances for Tottenham, scoring 28 goals.
Chris Jones grew up through the Spurs youth system and made his progression to the League team in August, 1974. In total he made 185 League and Cup appearances, scoring 42 goals in his nine seasons with the club. He was a skilful player but was unlucky in that he often got into good goal scoring positions but couldn’t quite turn them into goals. He helped Spurs avoid relegation in his first season and was a regular for much of the following season. He was part of the team which was relegated the next year but played his part as Spurs then won promotion. He scored 18 League and Cup goals in the next two seasons in the 1st Division but the arrival of Steve Archibald and Garth Crooks saw his first team opportunities diminish. His best goal scoring performance for Tottenham was an FA Cup 4th Round replay at Wrexham in 1979 where his hat-trick enabled Spurs to progress to the next round with a 3 – 2 win after extra time. He joined City for £110,000 in September, 1982 but after only three games in two months joined Crystal Palace. He also played for Charlton Athletic and Leyton Orient.
Bert Sproston was an England international full back who joined Spurs from Leeds United in June, 1938 for £9,500, a big fee at the time. Then the following November he was involved in a very unusual transfer. Having played nine games for Spurs, he was selected to play against Manchester City at Maine Road but on the day preceding the match he was transferred to City for £10,000 and played for them as Spurs lost 0 – 2. He had found it difficult to settle in London and remained with City until 1950.
Alex Steel was with City for eighteen months prior to joining Spurs in the summer of 1908. He was a half-back but only made one appearance for Spurs but that game has put him into the Tottenham record books. On that day in January, 1910 against Bradford City he became the third member of the Steel family to play for Spurs. He joined his brothers, Danny and Bobby, in the team, the only occasion when three brothers have played together for Spurs in a League game.
Alex Young who had a long, successful career with Everton joined Spurs in June, 1911 and scored on his debut. After three goals in his first two games he failed to score in the next three and was omitted from the team. He immediately demanded a transfer and went to City in November but was only there until the end of the season.
Bill Felton was a full-back who spent three years with Manchester City before joining Spurs in March, 1932. He played regularly in the team and captained the side to promotion in 1933 but lost his place midway through the next season and moved to Altrincham in the summer of 1934.
Neil McNab came to Spurs from Morton in 1974 at the age of sixteen for a fee of £40,000, signing as an amateur. He turned professional in the summer but had already made his League debut against Chelsea as a substitute in April, 1974 which, at the time, made him the youngest player to appear for Spurs in the League. Over the next number of seasons he played occasionally but in Spurs promotion season he played every game. The arrival of Ossie Ardiles and Ricky Villa in 1978 saw him lose his place following the 0 – 7 defeat at Anfield and he moved to Bolton in November, 1978. After being with a number of clubs he joined City in July, 1983 and had seven good years at Maine Road, playing probably his best football and helping them to promotion in 1989. He joined Tranmere Rovers in 1990 for two seasons.Clive Allen, the son of Les Allen, and one of Harry Redknapp’s backroom staff and had two and a half seasons at City after returning from a year in France with Bordeaux. He had joined Spurs from QPR in 1984 and scored twice on his debut against Everton but injury restricted him during his first two seasons. In 1986-87 season he set a new Tottenham record by scoring 49 goals including the first in the 1987 FA Cup Final defeat to Coventry City. That season, he was voted ‘Player of the Year’ by the PFA and Football Writers Association. He moved to France in March, 1988.
Clive Wilson, Bobby Mimms and Michael Brown played for City early in their careers and later joined Spurs but Paul Walsh who joined Spurs from Liverpool later joined City.