On the face of it there is nothing to connect winger Jack Lipsham, who played for Chester at the start of the last century, and current defender and midfielder Kevin Roberts. However the two players have the distinction of having the longest career span representing the club. In Kevin’s case this has spanned both Chester City and Chester FC, and is still ongoing, but both players have their first and last games for the club separated by 18 years. 

Jack played his first game in the opening game of the 1903/04 season, a Combination fixture against Witton Albion, with his last game coming after the First World War in March 1921. Kevin made his debut in the first away fixture of the 2007/08 season at Rochdale and is, of course, still a regular member of the team in 2024/25.

An outside left John Lipsham, better known as Jack or Jacky, was one of four brothers to play for the club. The most successful of these was Bert Lipsham who represented Chester in 1896 and 1897 and went on to play 235 times for Sheffield United winning an FA Cup winners medal in 1902 as well as an international cap for England. William, who was five years older than Bert, played twice for the club during the 1897/98 season while younger brother Tommy made his debut in 1901 and played at outside right until the end of 1904. The latter’s career overlapped that of his older brother Jack at Whipcord Lane while during the 1902/03 campaign both Tommy and Jack also played for Sheffield United Reserves where their brother Bert was in the first team. 

Jack was born in Chester in October 1881 and started his football career with Chester St John’s in the Chester and District League. At the end of the 1901/02 campaign St John’s were taken over by Chester and run as their reserve team with Jack a regular alongside brother Tommy. In September 1903 he made his first team debut at Whipcord Lane scoring one of the goals in a 5-0 win over Witton Albion. Over the next three seasons he only missed two Combination fixtures and was leading scorer in 1905/06. Although only 5ft 6in tall he was a well-built player and his speed down the wing and accurate crosses attracted the attention of First Division Liverpool who signed him in summer 1906. However, Jack only made three appearances for the Anfield club before returning to Chester the following year. 

By this time the club were playing at Sealand Road and Jack rarely missed a game as the club won the Welsh Cup for the first time in 1908 and the Combination League in 1909. By 1913 he had amassed more than 250 league games, a great achievement given that the number of fixtures per season ranged from only 24 to a maximum 38. In March 1913 the league fixture against Hyde was designated as a benefit for Jack and his colleague Billy Matthews in recognition of their great service and the princely sum of £82-10s was raised. Surprisingly Jack signed for Wrexham during summer 1913 but nevertheless remained a popular figure and returned to Sealand Road after the war when Chester became founder members of the Cheshire County League. He played his last game for the club in March 1921, against Stalybridge Celtic Reserves, at the age of 39 having made more than 300 first team appearances. Jack was also an enthusiastic cricketer and represented Chester St John’s while at the end of his football career he was a cashier clerk at the Army Pay Office and later became general manager of the Chester Steam Laundry in Boughton. He died in 1959. 

Of more recent vintage Kevin Roberts graduated from the Chester youth team and was given his debut by Bobby Williamson in central midfield, having just turned 18, in a 2-1 victory at Rochdale in August 2007. Two weeks later he went on to score his first goal in a 1-1 draw at Rotherham. Over the next three seasons he became an established first team regular making 81 Football League appearances in total. Following relegation he featured in all 28 Blue Square Premier league games in the aborted 2009/10 season and was a member of the team that lost 2-1 to Ebbsfleet United in the final game for Chester City.

Following the old club’s demise Kevin played for Cambridge United, Brackley Town (on loan), FC Halifax and Wrexham before returning to the Deva Stadium in 2019. Since then he has been a crucial member of the Blues squad and is fast closing in on his 200^th first team appearance. On current form it would be hard to bet against him extending his record into 2026 although it is worth noting that Connell Rawlinson played his first game for the club in the dying days of Chester City, against Oxford United in August 2009, and currently has a span of 16 years. 

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