The 35-year-old beat nine other singers from New Zealand and Australia to win the award, Newshub reported.
Often described as the Bledisloe Cup of country music, the Norfolk Island Country Music Festival brings together the winners of Australasia's top country music competitions.
Cummings made it into the invite-only event as reigning NZ Gold Guitar champion. He also won the CCMA Male Vocalist of the Year award at the Tamworth Country Music Festival in January.
"Winning this prestigious title is an awesome feeling", he says. "It's come with a number of additional obligations, however I'm loving every second of it."
GNews: Dunedin singer wins top trans-Tasman award - Newshub: Dunedin singer wins top trans-Tasman awardNewshu... https://t.co/tKNTnNdjA6
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The 10 artists had to perform three songs in front of a capacity crowd.
Cummings impressed the judges with his Gold Guitar-winning song 'Like A Cowboy'. He followed that with Keith Urban's 'Somebody Like You', and finished the set with a version of 'How Great Thou Art'.
Cummings is the second Dunedin singer to claim the sought-after award in recent years, with Kylie Price winning the prize in 2014.
