Rugby was played at RI from as early as 1886, but there is limited information on what happened in those days, save for a magnificent photograph of the rugby team of both staff and pupils, including C. M. Phillips, who would later became Principal of RI. The game did not seem popular, and it was only in November 1930 that attempts were made to revive it. Two teams were formed, and among the 30 players on the field were Dennis D’Cotta (later Judge of the Supreme Court) and John Le Cain (later Police Commissioner). The teams, which comprised staff and students, progressed well and by January 1931, an RI team was ready to play against the Singapore Cricket Club. Among the teachers who played in this team were Yapp Thean Chye and R. A. Goodchild. However, the early RI teams fared poorly, losing not only to various sports clubs but also other schools like Kota Rajah School.

In 1934, an all-student RI First XV was established with Bernard H. Y. Meggs, winner of the 1934 Queen’s Scholarship, as Captain. It is interesting that although inter-school rugby was played regularly between 1934 and 1941, no official rugby club or team was mentioned in the pages of The Rafflesian. What is clear from press reports is that by 1940, RI and St Andrew’s School were the top two rugby-playing schools in Singapore, and keen rivals on the pitch. In the last documented matches between the two teams before the War, St Andrew’s beat RI 17–0 at home, and 3–0 away.

In 1948, after the Japanese Occupation, the sport was revived in RI under the charge of an RI teacher, Gordon P. Darke, who had himself been an amateur rugby player. There were two teams: the First XV, and the Second XV. In November 1948, RI lost to St Andrew’s school in its first season, but improved significantly in the second season in 1949 under the coaching of Ng Wooi Kan of the Asian Rugby Union and L. V. Taylor of the Shell Sports Club. Michael Chua, who was captain of the First XV for both seasons, also played for Singapore Schools. It was only in 1950 that RI began beating its old rivals, and drew with strong teams like the Singapore Cricket Club.

Between the 1950s and the 1980s, RI and St Andrew’s took turns to dominate the sport, and between them supplied most of the players of the Combined Schools and national teams. For example, 11 of the 20-odd players of the 1960 Combined School’s team came from RI. The 1970s were a particularly good time for RI’s rugby teams as they regularly steamrolled their opponents with huge wins. In 1970, RI amassed an incredible 447 points against their rivals’ 12 points in the entire season.

Starting in the 1990s, other local schools began taking the sport seriously and began posing a serious threat to RI. The Anglo-Chinese School (ACS), which had not previously been dominant in the game, began beating both RI and St Andrew’s at the national level. By the early 2000s, sports journalists were pronouncing RI and St Andrew’s as also-rans in rugby, and members of the ORA started drafting an action plan to regain RI’s pre-eminence in the sport. However, ACS proved resilient and dominated the game thoroughly for the next two decades.

RI has not won a rugby B Division title since 1991, and did not win any C Division titles between 1994 and 2010. It was only in the A Division that RJC consistently won until 2010. In January 2010, a group of alumni ruggers under Rajoo Armudalingam and Cheng Soon Keong founded the Raffles Rugby Union as a way for alumni to assist in developing the sport in RI. (Raffles Archives & Museum, Raffles Institution)

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