|The roots of Darren’s career extend back to 1990 when he signed as a trainee at Tottenham Hotspur. Two years later he turned professional at Spurs, and debuted against Arsenal in August 1993. While at Tottenham he amassed 44 appearances and five goals, but also continued an illustrious career representing England in international football. Having 5 Schoolboy caps he went on to add 14 for the England youth team, and then a further 8 for the Under-19 side, playing alongside names including Sol Campbell, Paul Scholes and Robbie Fowler.
After a loan spell at Watford, Caskey moved to Reading in 1996 for £700,000 and made over 200 appearances for the Royals in five seasons, scoring 45 goals from the midfield. He then moved to Notts County in June 2001 and captained the side during a three-year spell with the then Division Two side, making 130 appearances. After a brief stint at Bristol City at the end of the 2003/04 season Caskey joined the Hornchurch revolution just as the 2004/05 season was getting underway, but moved to Peterborough United in December after the much publicised financial collapse of the Conference South leaders. Caskey was released at the end of his month contract by Peterborough after making four appearances on January 1st 2005.
Darren joined the Hawks for a month in February 2005 before jetting to America to play football professionally in the states.