[2] For the 2013 season, the competition was re-branded as the Ron Massey Cup in honour of the former coach, tactician, mentor and administrator.

The Ron Massey Cup is the latest in a succession of Sydney-based second tier, semi-professional Rugby League competitions.

The 'promotion' of two of the two biggest clubs Penrith Panthers (1966 champions) and Cronulla-Sutherland Sharks, at the conclusion of the 1966 season did not help the long-term stability of the competition.

During this period Wentworthville ("The Magpies") was the most successful club, competing in every grand final of the Second Division, winning a total of 8 premierships (including 5 in a row between 1967 and 1971).

Other teams in the new competition included the Guildford Owls, Mount Pritchard, Bankstown Greyhounds, Western Suburbs Magpies and the Hills District Bulls.

The Newtown Jets, who had been exiled from the New South Wales Rugby League premiership at the close of the 1983 season, were also granted admission into the competition in 1991 and became a successful club in their second life, winning 4 premierships (including 3 in a row between 1995 and 1997).Other teams who competed in the cup over the years included St. Marys Saints, West Wollongong Red Devils, Moorebank Rams (Bulldogs), UTS Roosters, Windsor Wolves, Cabramatta Blues, Sydney Bulls and the Kellyville Bushrangers The final Metropolitan Cup was contested in 2002 and was won by a newly formed club, the Sydney Bulls, defeating Ryde-Eastwood in the last grand final of the Metropolitan Cup.

The Jim Beam Cup was established in 2003 as part of another overall restructure of the NSWRL competitions operating in the levels below the NRL.

The Jim Beam Cup was intended to lay the foundations of a semi-professional 'State League' competition (similar to the Queensland Cup) and included four non-Sydney teams from the Central Coast (Erina Eagles, The Entrance Tigers, Ourimbah Magpies, and Woy Woy Roosters.)

During the 2012/13 offseason it was announced that Bundaberg Rum had withdrawn their sponsorship, and the competition would be renamed as the Ron Massey Cup, after the great Parramatta assistant coach.

2004 The St Mary's-Penrith Cougars left to focus on their NSW Premier League side, and were replaced by the Cabramatta Two Blues.

In terms of geographical spread four clubs were based in the Parramatta District (Wentworthville, Seven Hills, Cabramatta and Mount Pritchard), two on the Central Coast of NSW (Erina and The Entrance) and Canterbury-Bankstown (Chester Hill and Sydney Bulls) and one each in Penrith (Windsor Wolves), Manly-Warringah (Belrose), Illawarra (Shellharbour) and North Sydney (Asquith).

2008 In 2008, for the first time, an interstate team entered the competition, a Western Australia Rugby League representative side known as the WA Reds, with a view to developing the game in the state in order to secure a future NRL franchise in 2011–2012.

[7] The Entrance Tigers, who had claimed the 2007 title, unfortunately pulled out of the Jim Beam Cup due to the restrictions placed on gambling and smoking in clubs and pubs.

After the first round on 14 & 15 March, the Ron Massey Cup was suspended and subsequently cancelled due to the COVID-19 pandemic in Australia.

[9] In that single, first round the winning teams were the Kaiviti Silktails (40-16 on their debut), Concord-Burwood-Glebe Wolves (12-4), Wentworthville (18-14), St Marys (44-32) and Blacktown Workers (30-4).

On 28 September 2020, the NSWRL announced their intention to expand, from the 2021 season, the Ron Massey Cup to become a statewide competition.