Sheepbridge, Chesterfield born centre forward Jimmy Cantrell began his football career with Bulwell Red Rose in 1901 and played for Bulwell White Star in 1902 and Hucknall Constitutionals in 1903 before signing for Aston Villa in 1904, making his Football League debut that November against Notts County, scoring the third goal which proved the winner in a 4-2 victory at Villa Park. He played 51 matches, scoring 23 goals for Villa over the next 3 years including a hat-trick in a 6-0 win over Wolves in November 1905 and another in a 5-1 win against Sheffield United in December 1906, but found it hard to break into the first team on a regular basis in competition with the likes of Harry Hampton, before he made a big money move to Notts County in March 1908. At Meadow Lane he continued a goal every two games notching 65 times in 136 appearances over the next 5 years, including a 4 goal spree against Manchester City in February 1909 and a hat-trick against Arsenal in October 1909, before Tottenham Hotspur snapped him up in October 1912 for “a substantial sum” in the region of £1,600.
He made his Spurs debut at Manchester United on October 19th, then scored twice on his home debut against Aston Villa a week later. He grabbed his first Spurs hat-trick against Manchester City in December 1912 and scored 4 goals in a wild 5-7 defeat at Middlesbrough in February 1915. During the War, he guested for Notts County among other clubs. He continued to play for Spurs both sides of World War One but because of the interruption of the War he managed only 176 appearances, scoring 85 times for The Lilywhites in all competitions, winning The Second Division Championship in 1920 and then most famously the FA Cup in 1921, already aged 38. Cantrell remains the oldest outfield player to appear for Spurs when he played against Birmingham in April 1923 aged nearly 41. Leaving Spurs in the summer of 1923, he ended his playing career at Sutton Town before retiring in 1925.