[1][2] Born out of wedlock in Pietermaritzburg to a Welsh father and a black Saint Helenan mother, the dark-eyed and dark-skinned Llewellyn had an underprivileged upbringing in Natal, being considered of mixed blood.

While the racism of late nineteenth-century South Africa had led to other leading non-white players being omitted from representative sides, Llewellyn's ability to pass himself off as white in some cases (Wilfred Rhodes described him as "like a rather sunburned English player"), helped clear the racial hurdle to selection and he was chosen to make his first-class debut for Natal against Transvaal on 13 April 1895, where he took four wickets.

At the end of the 1898–99 series Llewellyn, perturbed by the actions of the selectors and seeking financial security, left South Africa to play for English county side Hampshire County Cricket Club as a professional, on the recommendation of South African teammate Major Robert Poore, an ex-Hampshire cricketer on military assignment.

He then toured Australia with the South African team, where his bowling served as fodder for Victor Trumper, before returning to England in 1911 to join club side Accrington,[5] thereby becoming the first Test cricketer to play in the Lancashire League.

During the apartheid period he was used to show that non-white cricketers could perform as well as their white counterparts, while modern day commentators have pointed to the erratic selection of Llewellyn for South Africa throughout his career as the result of prejudice due to his skin colour.