Cowes Football Club was formed in 1881, although competitive action did not take arrive until 1886 in the shape of the Hants and Dorset Cup. The Club joined the newly formed Hampshire League in 1895 and were crowned as its first ever Champions the following spring. In 1998-99 Cowes joined the Southern League alongside Tottenham Hotspur, Millwall, Bristol City and Swindon. However, financial difficulties prompted withdrawal from the League midway through the season winding up the Club.

In 1903 the Club was resurrected and nine years later celebrated moving to its current home Westwood Park by winning the Hampshire Senior Cup. By the mid 1920's the Club had become a formidable force and between 1926 and 1937 Cowes won the Hampshire League four times and Hampshire Senior Cup three times. In 1932 the Club lost to Newport in the final of the Senior Cup at The Dell in front of a crowd of 21,000, a record gate to this day. With four figure crowds regularly being atracted to Westwood, the main stand was erected in the space of one day before a local derby with Newport by the workers from one of the shipyards.

After winning the Hampshire Senior Cup in 1967, owes dipped into Hampshire Division 2 for the first time. The Division 2 title was won in 1975 and in the 1980's, Cowes merged with Whites Sports, becoming Cowes Sports. 1993 brought the first silverware to the Club in nearly 20 years when the Hants League Cup was won at Cams Alders, 120 supporters cheering the team to a 2-0 victory over New Street. Next season was even more exciting with Cowes and Blackfield & Langley going head to head for the League title. Blackfield held the advantage as we entered the run-in but a good run of results saw Cowes take the title and in the summer the Club was accepted into the Wessex League.

1994-95 brought our first IOW Senior Cup victory in nearly 30 years, a 4-3 victory over Newport in the semi-final preceding a 3-2 final win against Binstead. After a poor start in 1997-98, Cowes Sports climbed the table and could of claimed 3rd spot were it not for a poor run-in. Still, the season will be remembered for the run to the FA Vase 4th Round where Cowes faced 1997 runners-up North Ferriby who grabbed a replay victory after coming within 10 minutes of defeat at a packed Westwood Park. The 1998-99 season saw the side finish seventh in the Wessex League, but the campaign was crowned with a victory over Champions Lymington in the Wessex League Cup Final. The highlight since then has been the Combination Cup win in 2003-04, but this season the Club is perhaps, ready to record its highest ever finish in the Wessex League

Finishes in the Wessex League - 1994-95 15th, 1995-96 16th, 1996-97 9th, 1997-98 6th, 1998-99 7th, 1999-2000 9th, 2000-01 - 10th, 2001-02 16th, 2002-03 17th, 2003-04 14th, 2004-05 13th, 2005-06 16th, 2006-07 9th, 2007-08 9th