In 1911 Lady Elizabeth Clifford (the wife of the acting Governor of Ceylon, Sir Hugh Clifford) was interested in the annual rugby football fixture, Colombo versus Up Country, and expressed a wish that a match take place in Colombo on her birthday, 26 August, between teams representing the United Services and All Ceylon.

[1][4] Due to unforeseen circumstances the scheduled date was put off by a week and the first Lady Clifford Cup match (as it was originally called)[2] was played on 2 September 1911, with the United Services team defeating All Ceylon 25 points to 0.

[4][6] The Kandy Sporting Club made their first appearance in a Clifford Cup final in 1954, where they lost 21–5 against Ceylonese R & FC.

The format of the competition was also changed, whereby all 13 clubs had to play each other once on a home and away basis in alternate years and at the end of the league season the best eight teams competed in a knock-out tournament for the Clifford Cup.

[7] On that occasion the cup was won by Ceylonese Rugby & Football Club who defeated Havelock SC, 37–5.

In 1998 the SLRFU decided to suspend the competition due to security concerns relating to the ongoing civil conflict however they resolved to reinstate it the following year.

In 2019 the reigning cup holders, Kandy SC withdrew from the competition after being refused permission to play at their home ground, Pallekele International Cricket Stadium.

[1] The competition was suspended until 1926 due to World War I and during that time the original trophy was lost or misplaced.

In 2006 the Kandy Sports Club and Navy SC both withdrew from the tournament (Kandy due to dispute over the ground allocation and Navy as their members were called up for national service duty), the Cup was won by the Ceylonese Rugby & Football Club.