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Simon enjoyed a very successful playing career making over 300 appearances as a professional footballer across the football league. In the latter stages of his playing career he headed over to Singapore where he assumed the role of player / manager with Woodlands Wellington FC.

Since moving back to the UK in 2004, Simon has worked across both the senior and youth development phases, working with various clubs including Notts County, Watford FC, Charlton Athletic and more recently Peterborough FC.