James Gillen Robertson, born Glasgow, Scotland, December 17, 1944. A winger with pace and creativity, Jimmy Robertson left his mark on Scottish and English football in the 1960s and 1970s.
After an unsuccessful attempt to earn a professional contract with Middlesbrough, Robertson returned to Scotland, joining Cowdenbeath. It was at Cowdenbeath where his football journey truly began, and this move marked the first step in what would become a dynamic career. However, it was his next move to St Mirren in 1962 that truly catapulted him into the limelight. At St Mirren, Robertson developed into an exciting winger with a flair for creating chances and scoring goals. Over his 54 appearances for the Buddies, he found the back of the net 12 times. His performances drew attention from bigger clubs, and soon, English football came calling. In 1964, Tottenham Hotspur made a move for the Scottish winger, paying a transfer fee of £25,000, a substantial sum at the time. Robertson’s arrival at Tottenham Hotspur in 1964 marked the beginning of a period of great success and personal achievement. Spurs were one of the biggest clubs in England, and Robertson was thrust into a squad packed with talent. His time at the club was defined by several key moments, none more significant than his contribution to Tottenham’s FA Cup triumph in 1967. In the 1966–67 FA Cup season, Tottenham reached the final where they faced Chelsea at Wembley. Robertson etched his name in the club’s history by scoring the opening goal of the match, a crucial moment in what turned out to be a 2-1 victory for Spurs. His goal was a reward for his consistent performances that season and demonstrated his ability to perform on the biggest stage.
Moreover, during his time at Tottenham, Robertson became known for his pace and ability to beat defenders. His role as a winger was vital in Spurs’ attacking system, where he provided width and directness. Over the course of his Tottenham career, he made 181 appearances, scoring 31 goals—a respectable tally for a player operating primarily as a provider of assists from the wing. Yet, Robertson’s time at Tottenham would eventually come to an end. Despite his contributions, the club opted to move in a different direction, and in 1968, Robertson found himself at the center of a transfer that shocked many in North London. In a rare and controversial move, Robertson swapped Tottenham Hotspur for their fierce rivals, Arsenal. The transfer, which involved a straight swap for David Jenkins, raised eyebrows at the time. Players moving directly between the two clubs were uncommon, and the rivalry between Spurs and Arsenal only intensified the scrutiny surrounding the deal. Upon joining Arsenal, Robertson made his debut in a goalless draw against West Ham United in October 1968. The Scottish winger didn’t take long to make an impact, and he would go on to score eight goals in 59 appearances for the Gunners. Notably, Robertson became one of only two players to score for both Arsenal and Tottenham in the fiercely contested North London derby—a distinction that highlights his unique place in the history of both clubs. Despite these memorable moments, Robertson’s time at Arsenal was not as successful as his stint at Tottenham. Injuries and inconsistent form limited his appearances, and he eventually fell out of favor at Highbury. Nevertheless, his contribution to Arsenal, particularly in his first season, demonstrated his quality and professional attitude in the face of adversity.
In March 1970, Robertson’s Arsenal career came to an end when he was sold to Ipswich Town for £50,000. At Ipswich, Robertson found a new lease on life under the management of the legendary Bobby Robson. Ipswich Town, under Robson’s guidance, was a team on the rise, and Robertson became an important member of the squad. During his time at Portman Road, Robertson helped Ipswich secure their place in the First Division, ensuring survival in the 1969–70 and 1970–71 seasons. His experience and leadership were vital for the club, and although Ipswich was not yet challenging for top honors, they were laying the foundation for future success under Robson. In the 1971–72 season, Ipswich finished in a mid-table position, with Robertson playing a key role. However, just as he had found stability at Ipswich, another transfer beckoned. In July 1972, Robertson moved to Stoke City for a fee of £80,000. At Stoke, Robertson was reunited with Tony Waddington, a manager who appreciated his technical abilities and work ethic. He quickly established himself as a regular starter for the Potters, contributing to the team’s success in the early 1970s.
While Robertson’s time at Stoke City started promisingly, his career took a dramatic turn in December 1974. During a match against Coventry City, he suffered a broken leg, an injury that would significantly impact the remainder of his career. This injury sidelined Robertson for a lengthy period, and upon his return, he struggled to regain his place in the starting lineup. As a result of this setback, Robertson found himself on the fringes of the Stoke squad, and after two seasons without regular first-team football, he made the decision to leave England for a fresh challenge in the United States. In 1976, Robertson signed for the Seattle Sounders of the North American Soccer League (NASL). At a time when many British players were heading to the United States to extend their careers, Robertson saw this as an opportunity to experience football in a different environment. In his time with the Sounders, Robertson played 29 matches, bringing his experience and skill to the growing NASL. After his stint in the United States, Robertson returned to England to play for lower-league clubs, including Walsall and Crewe Alexandra, before retiring from professional football. His career had taken him across two continents and seen him play at the highest level, including an FA Cup final, North London derbies, and crucial First Division battles. On the international stage, Jimmy Robertson may not have enjoyed an extended career with Scotland, but he was capped once at the full international level, a testament to his ability. His international career may have been short, but it complemented his success at the club level.