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During the 1921-1939 period they were a very successful amateur club, winning every major trophy in Dorset Football on more than one occasion. They regularly played in front of crowds of two and three thousand and were virtually unbeatable on their own ground. After the Second World War they became a semi-professional club and joined the Western League, and in January 1949, they set a new ground record of 4,127 v Weymouth. During the 1950s and 1960s, whilst competing in the Western League, the Blues also enjoyed beating teams from higher Leagues in the F.A. Cup.
Of notable inclusion is the season 1964-65 when the Blues were runners-up in the league and also held famous cup giant killers Yeovil to a I - I draw at Grove Corner in front of a crowd of 3,069, and went down bravely at Huish on the following Wednesday 3 goals to nil in front of 6,005 people. At the end of the 1969-70 season the Blues sadly withdrew from the Western League to join the Dorset Combination League the following season, winning the combination title at the first attempt in 1970-71 and in the following few years appeared in the Dorset Senior Cup and on three occasions the final of the Dorset Combination Cup.
The 1993-94 season marked a watershed in the history of Portland United F. C for it was to be the last season that the Blues were to play on their infamous sloping pitch at Grove Corner as the Crown required the ground for mineral extraction and so the Blues were provided with a new ground a couple of hundred yards further up Grove Road. The old ground was formerly closed on 9th May 1994 with a celebratory game against their old rivals Weymouth F.C. m front of a crowd of in excess of 500, with the blues taking possession of their new ground in June 1994.
The 1997-98—season saw the Blues finish 2nd in the Keyline Dorset Combination League and also won the Combination Cup for the first time. Also it was the second year running that Portland were awarded the Trevor Williams Fair Play Trophy 1998-99 and the Blues had gone one better, achieving the Doubles winning the Keyline Dorset Combination League and the Combination Cup in the final at Swanage by 3 goals to ml against Parley Sports
Season 1999-2000 was another landmark in the Blues history, with the introduction of floodlights. On the pitch the 'Blues' continued where they left off last season, by winning the Dorset Combination League and Combination Cup, this time defeating Gillingham Town 4-3 after extra-time, at Days Park, Swanage in the Final
2000-2001 saw the 'Blues' lose only one match the whole seasons but had to be content with 2nd Place behind Hamworthy Recreation, and going out of the Combination Cup in the Quarter-Finals
Now for a whole new chapter, with Portland United being promoted to the Jewson Wessex League Division One.
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