The League was formed in 1955 and affiliated to the Sunday Football Association. At this time it consisted of one Division of nine Clubs who played each other once on a points basis for the Championship, then the two top clubs met in a Cup Final match.The first winners of both competitions were Riverside with Jets as runners-up.  

Following a meeting at "The Rifle Volunteer" in Oxhey, the League was increased for 1956/57 to fifteen Clubs who played each other twice in a League Championship with the top four Clubs competing on a knock out basis for the Cup. The League continued to grow with a Second Division being formed in 1957, and a Third Division in 1959. The League became affiliated to the London Sunday Football Association in 1962 and then to the Hertfordshire FA in 1964. In 1962 the three divisions were renamed; Premier Division, First Division and Second Division with a new Third Division added in 1964.

Continued growth resulted in the formation of the Fourth Division in 1965 and the Fifth Division in 1967, then after a gap of seven years, the Sixth Division was formed in 1973 together with the Sanonix Division, this latter Division however , only survived for three seasons. The Sixth Division had no competition between1976-1979 and 1980-1986and ceased once again at the end of 1997. The League decided that for the season 2001/2002, the Fifth Division would be discontinued, and since then the League have operated a Premier Division and Four other Divisions consisting of 44 Clubs, 6 of whom also have Reserve teams.

Whilst a number of Clubs have completed a season unbeaten , it was not until 1989/90 that a Club went throgh the whole season by winning all of their League matches. Although this had not happened before, when it did, not only did one Club complete this remarkable record, but two Clubs did it in the same season. That season Bedmond Only won the Sixth Division by winning all 20 League matches and Microgen won the Fifth Division by winning all 22 League Matches. As a result of their sucess, Bedmond Only were promoted two Divisions to the Fourth Division , and went on to win that Division in 1990/91 with 15 wins, 1 draw and no losses. In 1991/92 the Club won the Third Division with 17 wins, 1 draw and no losses, then continued their sucess in following years and eventually gained promotion to the Premier Division for the 1995/96 season. Only one other Club has had a more rapid rise to the Premier Division, namely OLd Garston Boys who entered the League in 2001 and gained promotion to the Premier Division for 2004/05. In 2004/05 Oxhey Estates became the third Club to complete the season by winning all of their League matches in the Second Division, and in the same season Pioneer, in their first season in the League, won 17 and drew 1 of their 18 League matches in the First Division. In 2008/09 Oakview FC won the Premier Division for the eighth time by winning all of their 16 League matches, the Club also went on to win the League Challenge Cup and the Herts FA Sunday Cup for the first time, thereby completing a remarkable treble in winning every match they played that season.Whilst other League Clubs have completed this treble none have ever done it by winning all their matches.

To date the worst Club record in the League was in 1969/70 when BAO finished bottom of the Fifth Division having lost all 18 matches, and scoring 18 goals with 190 against. The best record (other than Bedmond Only and Microge) was in 1961/62 when Woodside won the Third Division woth a record of 20 wins, 1 draw and 1 loss, scoring 200 with 18 against. During the 2001/02 season, Hammer FC ( longest members of the League between 1962 - 2015), completed the season unbeaten although they drew 4 League matches and as a result of this they completed a treble of Premier League winners, League Challenge Cup winners and Herts FA (Sunday) Cup winners. This treble was once again achieved by Oakview FC in 2008/09 and bettered Hammer's achievement by them winning all of their matches played in the season.

In the 2001/10 season, St Joseph's FC beat the record 9 wins of Evergreen FC by winning the Premier Division for the 10th time have also been runners up in 12 other seasons. They have also won the Challenge Cup on 13 occasions and been runners up 4 times and in 2006/07 they won this trophy for the 4th sucessive year equalling the Evergreen FC record. In 2009/10 season they completed the double for the 56th time, thus beating the record 4 times of Evergreen FC, previous double years being 1985/86, 2003/04, 2004/05 and 2006/07. In 2007/08 St Josephs FC won the the Challenge Cup for an unprecedented 5th consecutive year, thus beating Evergreen FC's record.

In 2014/15 Oakview FC won the the Premier Division for the 12th time, thus beating the record of St Josephs FC, they also won the Challenge Cup for the 6th successive year and therefore qualled St Josephs record. This also meant that Oakview FC had completed the Premier Division and Cup double for the 6th time, thus beating the record of St Josephs FC.

Over the years, the League has entered a Representative Team in the Herts FA Inter League (Sunday) Cup, records show them to have been winners in 1968/69, 1970/71, 1973/74, 1975/76, 1980/81*, 1983/84*, 1998/99, 1999/2000, 2001/02, and runners-up in 1990/91*, 1991/92, 1992/93, 1994/95, 1995/96, 1996/97, 2000/01 and 2002/03 (final competition season).

*(entered as S W Herts Sunday League)

At the end of the 2015/16 season it was agreed with the Olympian Sunday Football League that the two Leagues should join together and this was reflected within the new Competition Constituition for the 2016/17 season allowing the League to run Six Divisions.  

Updated April 2017.