Olliff was a leg-spinner, "a little man with a big break, who did amazing things with the ball on a sticky wicket, to the utter confusion of even the most experienced batsmen of the day".

[1] Only five feet three inches tall,[2] he made his first-class debut for Auckland on Christmas Day 1903, taking 3 for 45 and 4 for 35 against Wellington.

His most successful season came in 1909–10, when he was the leading New Zealand wicket-taker with 23 wickets at an average of 19.47[5] and Auckland won all three of their Plunket Shield matches.

A well-known ex-player also presented the bowler with an order on a local firm of mercers for a hat, with a stipulation it must be a belltopper.

A benefit match was held for him in January 1914 between Auckland and the New Zealand Nomads, a team of country cricketers from the North Island.