Legendary Super Impose put the Freedman brothers down in Thoroughbred Park's history books in 1992 and almost three decades later they could lift another Canberra Cup on the same hallowed turf.
Richard and Michael Freedman are set to return to where their racing careers began after Cinquedea won the inaugural Canberra Mile (1600 metres) to qualify for the listed Canberra Cup (2000 metres) on Friday.
The four-year-old gelding broke the track record to claim the $150,000 race, beating the Jason Coyle-trained Valentino Rossa by 0.99 lengths.
The first two runners home get a ballot exemption into the Canberra Cup, meaning Valentino Rossa will join Cinquedea at next month's Black Opal Carnival.
Will Freedman, the son of Richard Freedman, says winning the first edition of the Mile is a great honour for the family given their long history in the region.
"The Canberra Cup holds sentimental value for our family and having a runner in with a shot is very special for my father, uncle and the rest of the family," Freedman said.
"All the brothers were local Yass boys and spent many years coming to the Canberra Cup, so they'll be pleased to now hold the track record for the mile.
"It's a tough mile here in Canberra and it takes a good horse to win, so I'm hopeful this horse is going places."
Cinquedea has now had four podium finishes from six starts this preparation and will likely go straight into the Canberra Cup without another race.
The Freedman stable will give him a light week in the paddock before reassessing his lead up to the carnival.
"He isn't going to gain any more fitness. We'll just have to play it by ear, he's a quirky horse," Freedman said.
"He did remarkable well for a horse that has had his sixth start. He's probably right at the peak of his powers this preparation and hopefully he can put one together in a couple of weeks."
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Snowden-trained Aftermath and Bjorn Baker's Lady of Luxury earned a spot in the Black Opal Stakes, with the former horse finishing first by a narrow 0.16 lengths to win the 1000 metre Preview.
Gold Touch just held out Matthew Dale's Sausedge in the Federal (1200 metres), with both gaining ballot exemption into National Sprint.
The Luke Pepper-trained mare stormed home on the straight to beat Sausedge by 0.11 lengths and claim the $40,000 race.
John Sargent's Foxborough defied being wide to gain a berth in the Canberra Guineas, while Sirmaze gained the second ballot exemption.