One is a tycoon who formerly ran a tabloid famed for breaking outrageous "news" including the discovery of a World War II bomber on the moon.
The other is a tycoon probably best known now for campaigning against cats.
In one corner, meet West Ham United chairman David Gold, 77, here for the football club's first visit to New Zealand. In the other corner, is Wellington Phoenix part-owner Gareth Morgan, 61.
Gold dug himself out of poverty to make a fortune in lingerie with Ann Summers and Knickerbox and, with his brother Ralph, published porn magazine Rustler, and tabloids Daily Sport and Sunday Sport. The latter was known for headlines such as "Gordon Ramsay Sex Dwarf Eaten By Badger".
Gold also once owned an airline, Gold Air International.
He enjoys travelling by helicopter, sometimes landing his chopper on the pitch as players train, sending them scuttling to one side of the ground.
In Celebrity Number Plate Stories, Gold is described as a keen young football fan, who at 15 was offered an apprenticeship with West Ham, the team he always loved.
"Now imagine the anguish that followed," the story continues, "when his father refused to sign the forms, insisting David should complete a bricklaying apprenticeship instead."
Gold had the last laugh - six decades on, he owns a 35.1 per cent stake in the Hammers.
Philanthropist and pornographer David Sullivan, a fellow Sunday Sport alumnus, owns 51.1 per cent.
Morgan, an economist, philanthropist and protector of native birds, has also faced a battle for hearts and minds.
"I do not hate cats", he told NBR last year, after a wave of hatred crashed down on him.
For the record, Morgan has other interests, including travel and motorcycling. He was the most high-profile of the six men who bought the Phoenix in late 2011.
Gold said he's looking forward to meeting Morgan and the Phoenix management.
"This is a once in a lifetime opportunity for me to learn from them," he told the Herald on Sunday. "I'd be disappointed if we didn't sit down over a bit of lunch to discuss what we're doing."