When Holland was 15 he met Colin McCool, the player coach at Belmont Club. When he was 19 he played for Northern NSW against Mike Smiths' 1965–66 MCC team. He represented Northern NSW in 1975–76 against the touring West Indian side as an opening batsman.

1978–79

Holland made his Shield debut in 1978–79.

1980–81

Holland's 4–30 helped NSW beat WA by an innings. He was left out of the McDonald's Cup side but kept in the NSW Shield team. He took 5–82 against South Australia.

1981–82

Holland took six wickets in his first Shield game and four in his second, causing people to discuss him as a test prospect.

1982–83

Highlights of this summer included 3–16 against Queensland.

1983–84

Holland took his best figures to date, 7–56 against South Australia. There was some talk this would put him in contention to replace the Australian spinner, Tom Hogan.

1984/85 season: West Indies

Holland began the 1984–85 Shield comp well with four wickets against South Australia.

Holland made his Test debut in the Second Test of the 1984–85 Australian season against the West Indies cricket team in Brisbane. He was relatively unsuccessful, taking 2/97 and scoring 6 and 0 as Australia suffered an eight wicket defeat.

He was retained for the Third Test in Adelaide, but after taking match figures of 2/163, he was dropped.

Holland went back to New South Wales and continued the form which had gained him Test selection in the first place. This included a tour match victory over the West Indies, after which both Holland and Bennett were selected for the Fifth Test at the Sydney Cricket Ground. The selectors had felt that the uncertain performance of the Caribbean batsmen during the tour match showed that they had a weakness against spin bowling, and introduced a "horses for courses" spin oriented attack on a dry Sydney pitch.

The West Indies had crushed Australian opposition throughout the summer, winning the first three Tests by an innings, eight wickets and 191 runs respectively. Furthermore, in the fourth Test, Australia had slumped to 8/198 chasing 370 to narrowly avoid defeat when time ran out. With pundits expecting another Australian failure, they won the toss and amassed 9/471. The West Indies were reduced to be all out for 163, with Holland taking 6/54 including Viv Richards, Desmond Haynes, Larry Gomes and captain Clive Lloyd. Forced to follow on, they fell for 253 in the second innings with Holland taking 4/90 to complete a ten wicket match haul. The New South Wales pair perplexed the tourists, taking 15 of the 20 wickets, as Australia took an unexpected innings victory. Following his spin success at the SCG, he was selected to make his ODI debut on the same ground against the same team in the subsequent triangular tournament. With 0/50, he was the most expensive bowler in the match and did not play again in the season.

1985 Ashes

He was selected for the 1985 Ashes tour to England, but only had sporadic success. In the ODIs, he played only in the first match at Manchester. He took his only ODI wickets with 2/49 as Australia won, but was the most expensive bowler and was dropped.