Toby Redwood came through the youth ranks and made twenty league appearances for Exeter City between 1991 and 1994. After his release he played for Dorchester Town and a number of other clubs towards the top end of non-league football before becoming head of academy education at Southampton.

Toby, son of Barry Redwood (who made two first-team appearances in the 1960s), joined Exeter City on schoolboy forms in November 1988 and became a trainee in 1990 before turning professional in June 1992. A native of South Devon, Toby made his debut whilst still a trainee in the home fixture against Torquay United in September 1991.

Never a regular in the first team, Toby clocked up twenty league appearances - 15 starts, 5 from the bench - over a three-season period. 

Leaving St James’ Park Toby signed for Dorchester Town. and settling in the Hampshire area, went on to play for Basingstoke Town, Taunton Town, Weymouth and Chippenham Town before joining Winchester City in December 2003. After later appearing for AFC Totton, Lymington & New Milton and Poole Town, he briefly coached Hythe & Dibden.

Appointed head of academy education at Southampton in 2009, Toby was still in post in 2023.