Wigley and his wife Carol raced star filly Canterbury Belle, who won the Classic for trainer Dave Kerr in 1984.
Now Matchmaker , who Wigley and his training partner Kayla Milnes produced to win the Listed Canterbury Belle Stakes (1200m) at Riccarton last month, has a gilt-edged chance of emulating one of Canterbury racing's great performers.
"Canterbury Belle was strong and powerful and she'd grind them into the dirt, whereas Matchmaker may have a better turn of foot but she's probably no Canterbury Belle," Wigley said.
"It was huge for us at the time owning a filly as good as Canterbury Belle. My father (Sandy) said at the time the problem with her is that we had a good horse too young and we'd spend the rest of our lives trying to find one as good, and he was probably right.
"It's always been on my bucket list to own and train a 1000 Guineas winner and while I don't own her, it's probably the next best thing training one for your son and daughter-in-law."
Wigley's son Gus and his wife Bianca bred and race Matchmaker, these days retaining a 50 percent holding after Sydneysider Manoj Wanzare bought into her earlier this spring.
The Makfi filly, who will join Sydney trainer Chris Waller after Saturday's race, is a $19 chance with TAB bookmakers after drawing barrier 12. Troy Harris is booked to ride.
"We'll have to ride for luck. Both her wins she's had cover then pulled out for clear air - and that will help her get the 1600m too," Wigley said.
"There's nothing to compare the South Island form to the Soliloquy Stakes (Gr.3, 1400m) form except through the TAB market, which is favouring the Soliloquy form. It's a pretty open race.
"She had a nice gallop between races on Saturday with Fashion Shoot. They didn't go overly hard but she did enough with the big crowd there.
"She galloped on the Rangiora track on her own on Tuesday and went to Woodend Beach on Thursday and again today (Friday). She did strong work yesterday over a mile and then walked in the surf.
"It's up to the luck of the race now. If she runs up to her best form and can unleash, we'd be disappointed if she doesn't run in the first four."
Wigley, 71, quips he's "aged a bit" since the Canterbury Belle days but that experience has helped mould him into the astute horseman he is now.
He recalls the offers to buy Canterbury Belle in the wake of her 1000 Guineas win which rose from $300,000 to $500,000 within hours of the race and soon afterwards led to a $1.5 million offer from American interests, which fell through.
"Carol was dead against selling. She didn't want us to be the young couple that everyone said had just come into some money."
The upshot was the Wigleys got to experience further Group One success in the Stradbroke Handicap (1400m) at Eagle Farm. Canterbury Belle won 10 of her 21 starts before the Wigleys retired her and bred from her as a broodmare.
Wigley and Milne will shoot for further stakes success at Riccarton with promising Capitalist filly Mozzarella tackling the Listed Frantic Bloodstock Welcome Stakes (1000m), while Blackbook is a leading chance in the Vernon & Vazey Truck Parts Premier (1400m).
"Mozzarella was going to the start and got cannoned into and got away from Sam (Wynne, jockey). She was cleared to start but gave the winner a five-length start. She was only five lengths away from him at the finish so we think she's a real show," Wigley said."Blackbook is probably our best winning chance. She's racing really well and she's got a good inside draw and Lisa Allpress on. She should be really competitive."