Rugby was officially added to the school's games in 1929 under Headmaster Hubert C. Stone. At its inception, it was not intended to replace Football, which was then the primary winter game; rather, it was seen as an opportunity for boys who did not excel at football to find a sport where they could succeed.
In these early years, the sport faced physical challenges, as Front Field was not as level or open as it is now. Until 1932, boys were forced to play "up and down sloping ground" in the front field until several trees were felled to allow a proper pitch to be laid across the area. Despite these limitations, by 1932 the school was in its third season of "rugger," and the game was described as having found its "rightful place" in school life, with even the Lower School boys participating in practices. However, the school's small playing field remained a handicap when teams played away matches on larger, full-sized regulation fields. The development of rugby was closely tied to the House system, which was established around 1928-1929. House matches became a "vital force" in building school spirit: Foster House won the Rugby-Football Competition in 1932, its very first year as a house and the Morris Cup was established as the primary trophy for inter-house rugby. By the late 1930s and early 1940s, Dudley and Foster houses emerged as strong contenders.
This picture taken in 1936 shows the school team. On the Captain’s left shoulder is George Grey who was Headboy, and whose name appears in the Great Hall. He came to OSH as a boy from a Single parent family, as his Dad was one of the first people to be killed in a car accident. He prospered after school, sending all his boys to Private school. The children all did extremely well, and one owns the Gtech company in Worcester.