Though it has its origins as a humble, rural sport, the handball game of Fives was adopted (or co-opted) by Eton and Rugby in the 1870s and developed an elitist reputation. The game spread to other schools like Charterhouse, Harrow, Westminister and, by the 1880s, to the newly refounded Portsmouth Grammar School, where the first Fives court was built in the playground in 1881.

It seems likely,according to the memories of Col R F Tipper (OP 1934), that this was a Rugby Fives court. The game was popular, but only four boys could play at any time. By the 1930s he recalled, “I think we had two Eton courts in the new school (the current main site) and one Rugby court on the old (the current Upper Junior school). The only equipment needed is a ball and one padded glove (though often the bare hand was used). The game can be enjoyed immediately without any tuition and is an ideal way of letting off steam and getting maximum exercise in the minimum time – ideal for morning break and lunch hour.” In fact, three Eton courts were built between 1926 and 1930. Reports of matches appear in the Portmuthian in the 1930s; in December 1932, for example, it was reported that the school was outplayed by Bedales because the PGS players were more used to Eton fives. 

Derrick Hughes (OP 1937) and Ron Larkham (OP 1937) recalled that the courts "consisted of a buttress and two levels of the floor. The game was played with a small, hard ball and if you were lucky you had a special leather glove. It was a fairly hazardous sport with many minor accidents, first-aid being available from Thorn, the benevolent school porter. I doubt if health and safety would allow it now."

In the spring of 1937, the House Fives Captains encouraged the entire Third Year to take up the game. However, other demands on the use of the school site led to the courts being demolished, the three Eton fives courts making way for a new Science block in 1953 - now the site of the Bristow-Clavell Science Centre.   

Very little trace survives of the playing of Fives at PGS, other than in the memories of more senior OPs and two surviving Fives gloves that have been donated to the school archive.