Initially formed in 1881 and in 1898/99 they played in the top Division of the Southern League against the likes of Tottenham Hotspurs, Millwall and Bristol City but poor results and financial difficulties saw the club fold in mid-season. They reformed in 1903 and moved to their current home in 1912. In 1932 they lost to fellow Island side Newport in the Final of the Hampshire Senior Cup at the Dell in front of a crowd of 21,000.

They reached the 4th Qualifying Round of the FA Cup in 1963 and the 4th Round Proper of the FA Vase in 1994, the same year as they joined the Wessex League. The League Cup was won in 1999 and they have won the treasured Isle of Wight Gold Cup on over twenty occasions, the most recent being in 2012. Gained Charter Standard in the 2012/13 season.

The Club have had a number of players who have gone on to make their mark in the Professional game.

JAMIE LAWRENCE: ( Sunderland, Doncaster Rovers, Leicester City, Bradford City, Wigan Athletic, Walsall, Brentford and the Jamaica National side.) Currently Manager of Combined Counties Side, Cobham.

JAMES HAYTER: (Bournemouth, Doncaster Rovers, Yeovil Town)

LEE BRADBURY: (Portsmouth, Exeter City, Manchester City, Crystal Palace, Birmingham City, Portsmouth, Sheffield Wednesday, Derby County, Walsall, Oxford United, Southend United and Bournemouth). Currently Manager of Conference side Havant and Waterlooville having previously managed AFC Bournemouth.

GARY ROWETT: Cowes Under 18 ( Cambridge United, Everton, Blackpool, Derby County, Birmingham City, Leicester City, Charlton Athletic and Burton Albion). Is currently Manager of Birmingham City has also Managed Burton Albion.