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Cummings (35) has won two major country music awards in the past year - the CCMA Male Vocalist of the Year at the Tamworth Country Music Festival in January, and the New Zealand Gold Guitar Senior category in Gore last June.
Cummings' latest challenge is the Transtasman Entertainer of the Year competition.
A key event at the 24th Norfolk Island Country Music Festival, it is described as the Bledisloe Cup of country music.
"I'm one of five New Zealanders who have been invited and we go up against five Aussies. Each of us sings three songs and the judges pick the winner based on our performances,'' Cummings explained.
"In addition, we do a range of guest spots and showcases as part of the festival.''
The festival begins on Monday.