Born in St Vincent, Ollivierre initially played first-class cricket for Trinidad; he was selected to tour England with the West Indies team in 1900.

[3] Initially, Ollivierre played for Trinidad; he made his first-class debut against an English touring team in March 1895 at the age of 18.

[5] In non-first-class cricket, he continued to represent St Vincent,[5] and impressed critics when Barbados played the island in 1897.

[5] According to the review of the tour in Wisden Cricketers' Almanack, Ollivierre was the team's best batsman, and his innings against Leicestershire was one of the best of the season.

[9] During the tour, Ollivierre agreed to play for Derbyshire and remained in England to begin the two-year process of qualification for the County Championship.

[notes 2][4] He was employed by Samuel Hill-Wood, a businessman and politician from Derbyshire, to work in his office in Glossop,[6] where Ollivierre lived.

[12] Against Essex, he made the highest score of his career,[5] when, according to his obituary in Wisden, "he was the dominating figure in a remarkable match".

[14] The match report in the 1905 edition of Wisden noted: "In defeating Essex, Derbyshire accomplished the most phenomenal performance ever recorded in first-class cricket ... [Their] achievement has no parallel in the history of the game.

[1] However, he continued to play club cricket in Yorkshire and, annually between 1924 and 1939, spent time in the Netherlands coaching in schools.

He was a more heavily built man than the slim Ranji of the days when we were young; but his strokes and his movements had real grace.

"[8] A correspondent in the Observer in 1931 remembered Ollivierre as a "great batsman",[11] while Neville Cardus, writing in 1920, named Ollivierre among a list of top-quality batsmen who did not do themselves justice at the highest level: "Geniuses who have just lost their way ...every one of them in possession of an excellent enough record in county cricket, but every one of them really intended by nature to wear the most precious laurels the greatest of games has to offer".