The top award this year went to the Robinsons Bay Grove Blend - a commercial medium blend from Akaroa.
The head judge of the awards, Peter Olson from Australia, said he has been assessing oils from Australia, California and New Zealand, and the New Zealand extra virgin oils were among the best this season.
Kate Bunny said the variety they entered, picholine, was not the most prestigious of olives, but it had a complex flavour that appealed to the judges.
"It's very fruity, with lots of complexity," Mrs Bunny said.
"Different sorts of fruits keep it moving on the palate; this year it's very 'chilli' at the end."
The variety comprises a third of the grove's trees and, due to a light harvest this year, was the only one they entered.
However, it was again strong enough to be best in its class, commercial intense single.
Mrs Bunny said winning the award "just changed it for us last year" with approaches from boutique food marketers and a recent dinner with the Taiwanese Business Association in Auckland.
The best-flavoured oil, Juno Olives lemon agrumato, was made the "pure traditional way", according to Karen Juno of Juno Olives.
An agrumato is made by pressing the olives together with other fruits - in this case lemon - so that the oil comes out blended.
"We take the risk and put the two together and hope it comes out right," Mrs Juno said.
"It's been quite an experiment with percentages."
Juno Olives also took two silver medals, with its boutique medium blend, leccino and its commercial intense single, a manzanillo.
Craig and Ruth Leaf-Wright won three silver medals in the flavoured category with Leafyridge Roasted Garlic and with commercial medium blends Frantoio/Leccino and Leafyridge Grove Blend.
Other Wairarapa silver medals went to Mike & Joy Cooper with their Molive Gold, Helen and John Meehan with Olivo Extra Virgin, and Steven and Chris Price with their River Grove Frantoio.
Wairarapa, New Zealand's largest olive-growing area, won 29 of this year's 69 medals.