Since retirement, Caskey has coached at Ilkeston Town, later taking on the role as assistant manager at Wrexham before a similar spell at York City.

[1] A central midfielder, he started his career as a trainee at Tottenham Hotspur, but failed to live up to early potential.

[2][3] He went on to have notable spells at Reading and Notts County, also playing for Peterborough United and Rushden & Diamonds,[4] where he scored once against Shrewsbury Town.

[6][7] He captained the England national under-18 team that won the 1993 UEFA European Under-18 Championship, scoring the winning penalty kick in the 1–0 victory against Turkey in the final.

[11] Caskey had already been assisting Mills after his appointment at York City, working without a title or a contract.