Big Gamble preceded his 1979 Wellington Cup win with a second to Good Lord the previous year and he ran fifth in the 1981 edition.
Sampson's two Wellington Cup starts have resulted in a third to Mister Impatience in 2016 and a second to Magic Chai two years ago and, after a last-start encouraging second behind Beauden in the Listed Marton Cup (2200m) at Awapuni, Mathews believes the son of Dubai Destination has a good chance.
"Just to have another Wellington Cup runner will be pretty awesome and I think he can win it.
"He's very fit and [jockey] Johnathan Parkes is back on him."
Raced by Mathews' wife, Lorraine, and Janice Street, Sampson has won 11 of his 76 starts and earned more than $528,000 in prizemoney.
His latest win was an 8 -length triumph in the Listed New Zealand St Leger (2600m) last March and between times Mathews and his wife have campaigned him in Australia.
"He didn't win a race, but he went some top races and ran second in the Ipswich Cup [Listed, 2150m]. He paid his way," Mathews said.
Sampson's Australian campaign ended with a fifth in the Listed Queensland Cup (3200m) at Eagle Farm last July and he reappeared on the NZ scene when winning over 1400m in Foxton trials in November.
The Marton Cup was Sampson's fourth run this campaign and followed an eighth in the group three Manawatu Cup (2300m).
"It's best to space his races," Mathews said. "Us old boys need our nana naps."
- NZ Racing Desk