The national award judges noted Matheson's casual, relaxed style, describing him as an extremely capable manager who ran the farm for an overseas-based owner.
"James is goal driven and has achieved many goals he set himself years ago. He places staff as top priority and encourages them to better themselves.
"He's basically jumpstarting his staff, giving them a head-start on other people in the industry,'' judge Malcolm Scott from Westpac said.
Matheson, who also won the Meridian Energy leadership merit award, won $11,400 in prizes.
Colin and Isabella Beazley, from Northland, were named 2019 New Zealand Share Farmers of the Year, Matt Redmond (Canterbury) was Dairy Manager of the Year, and Nicola Blowey (Canterbury) was Dairy Trainee of the Year.