As a player, he was a defender who notably played in the Premier League for Swindon Town and West Ham United.

He had spells as assistant manager at Barnet, Brentford, Milton Keynes Dons and Leicester City.

Whitbread has frequently worked under the managership of Martin Allen and was most recently assistant manager at Chesterfield.

[2] Following Swindon's relegation from the Premier League, Whitbread joined West Ham United in August 1994 in part-exchange for Joey Beauchamp.

[7] He made 18 league and cup appearances before a knee injury sustained in training in December 2001 ruled him out of the rest of the 2001–02 season.

In December 2011, he was named head coach of Puerto Rico Islanders, now playing in the North American Soccer League.