Rugby has been an integral part of Otago Boys' High School since 1871 when mention of the first game played is reported in the local newspaper. It is highly likely however, that the oval ball was being kicked around prior to this but as no records exist the year 1871 is taken as the start of the club. The game referred to was against a University team and lasted for 3½ hours on the first day and a further 3 hours on the following Saturday - for it to be declared a draw.

Between 1871 and 1883 the boys played against local clubs with a number of the players gaining higher honors through provincial and New Zealand representation.

1884 was a benchmark year as the first game against Christ's College was played. This came about almost by accident as the visitors had been invited to play another local team. The Christ's College Headmaster would not accede to this invitation but gave his approval for a game against Otago High School. As they say - the rest is history - as these teams have met annually since then.  The sequence was broken in 1918 because of snow, 1923 with the influenza epidemic and 1944 due to wartime travel restrictions. 2010 saw the 124th encounter between these two rivals - perhaps not the longest continuous interschool but surely one of the longest.

The intervening years have seen regular fixtures against Southland B.H.S., Waitaki B.H.S., Christchurch B.H.S., Kings H.S. and Timaru B.H.S added to the interschool programme.

Like a lot of New Zealand high schools, Otago Boys' sees itself as something of a nursery for future provincial and national representatives and over the years has produced its share with Byron Kelleher, Wyatt Crockett and Richie McCaw being our three most recent All Blacks. Richie has reached the pinnacle of every rugby players career by being named as All Black captain.

In 2009 a new competition was introduced. This competition, the Highlanders 1st XV Competition embraces 12 teams from high schools across the Highlanders franchise in Otago, Southland and North Otago. For the first time since the club's inception the 1st XV was not involved in the Dunedin club competition.

Versus Played Won Lost Drawn Result to:
Christs' College 125 66 53 6 2011
Christchurch B.H.S. 95 41 52 2 2011
Southland B.H.S 97 39 47 11 2011
Waitaki B.H.S 66 45 19 2 2011
Kings H.S. 72 47 21 4 2011
Timaru B.H.S 85 48 34 3 2011
Totals 539 285 226 28 2011