"I must say she has the most gorgeous smile in the whole world. Will you tell her that from me and we'll have a drink together when I get down there."
Despite the obvious amorous overtones, Gayford kept his cool, saying: "I'll text her right now, where's my phone?"
Stewart and Gayford also found common ground when discussing having a famous partner.
"I've loved New Zealand and Australia, of course, because I've been touring down there since the early '70s, but of course you know I was married to Rachel Hunter," Stewart told Gayford.
"I must admit, whenever Rachel did go down there, I had to walk two paces behind like the Duke of Edinburgh does with the Queen. She was more important than I was."
Gayford laughed and replied: "I know how that works."
Yesterday afternoon, Stewart's performance of his hit song Sailing, recorded while floating down the River Thames in London, was beamed into Auckland's America's Cup Village and around the country.
New Zealand's tourism bosses saw the 36th America's Cup as an opportunity to send a message of unity and togetherness to America's Cup competitors and their fans around the world.
"Aotearoa's warm welcome and manaakitanga was on full display today, as we cheered on our international friends and became back-up singers for our mate Rod," said Tourism New Zealand, Interim Chief Executive, René de Monchy.
The iconic rocker had this to say: "I have a great big soft spot for New Zealand since two of my children are Kiwis and so I'm pleased to be a part of the America's Cup, joining Kiwis to send this message of togetherness out to the world. I hope my performance of Sailing brings some joy to fans in these challenging times."
The America's Cup match is a best-of-13 series, with the winner being crowned champions and awarded the Auld Mug. The racing window for each race day will be around 4pm-6pm.