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Stenhouse was on the reserves' bench when Tech Old Boys, as they were known then, lost 1-3 to Auckland side Mt Roskill in the 1964 Cup final.
His father, Alex, played in two unsuccessful attempts by Mosgiel to lift New Zealand football's greatest prize.
It lost to Wellington side Waterside 0-4 in 1938 and 2-6 to the same club in 1940.
Clearly, the family does not have the greatest track record in the Chatham Cup, but Stenhouse laughed off suggestions of a family curse and will be in Auckland to support his side play East Coast Bays.
"They've done very well to get there and they need all the support they can get," Stenhouse said.
The 66-year-old is a life member of Dunedin Technical and is also the club patron.
He continued to play football until he was forced to hang up the boots six years ago because of a dodgy ankle, which now requires a brace.
He decided to make the trip because, basically, he was fed up with losing.
"My father played in two finals for Mosgiel and lost both, and I went to the '64 final and we lost that one. And I didn't get to the win in 1999."
Dunedin Technical shocked a powerful Waitakere City 4-0 in the final that year, upsetting most predictions.
Stenhouse was not there to bring his club bad luck but, to his credit, he was not at the final a year earlier when Dunedin Technical received a 5-0 drubbing by Central United.
"That's my one saving grace," he said, chuckling.
In the 44-years since the 1964 final, Stenhouse has forgotten much about the day.
"I guess you tend to remember more if you get a run. I was a reserve and in those days you virtually had to get a doctor's certificate to come off.
"Probably the experience of the Auckland team told on the day. A lot of the Tech team were in their early 20s and possibly - I don't want to say we were overawed because it sounds terrible - but in hindsight we probably were."
There were no losers' medals but "the team was presented with the match ball after the game but I don't think it even got back to Dunedin".
Mt Roskill left shortly after match to travel back to Auckland which Stenhouse said was disappointing.
So much of sport is about socialising, he said.
On the trip back to Dunedin the team made a stop off in Christchurch.
"We had to play an invitation side in Christchurch on the way home after a night on the bash. They turned out virtually with a Canterbury team."
Stenhouse remembers one team-mate foolishly electing to head the ball and having to take a lie-down.
Stenhouse lives in Alexandra these days and is semi-retired.
Whenever he is in Dunedin he makes sure to catch a game at the club.
He saw Dunedin Technical beat Queenstown in the resort town last weekend and thought it looked a bit rusty.
But he is confident his side can do well in the final.
"The way they've played the last two matches against teams from the North Island they should go well."