It was a high-five Hall of Fame jockey Sandy Hawley won’t ever forget, a win that came 40 years ago in a high-profile race, and one that capped a remarkable run for the revered rider.

In the days leading up to the running of the 1974 Woodbine Oaks, there was plenty of talk as to whether Hawley, who had won the past four editions of the 1 1/8 mile race for Canadian-foaled three-year-old fillies, would deliver a fifth consecutive score.

Perhaps the only thing going against Hawley was the colour of his horse: no grey had ever won the Oaks since its inception in 1956.

But, when the gates opened at Woodbine on June 22, 1974, Hawley marched Trudie Tudor, a daughter of Tudor Grey, to the lead. And that’s just where the duo would stay, wiring the field, giving the man in the irons his fifth-straight Oaks triumph.

It was to be the only Oaks race with the track listed as “slow,” but the track condition didn’t hamper the winning pair’s primetime performance.

“She was a really neat filly,” said Hawley, of the Douglas Banks-bred star, who won the Sovereign Award as Canada’s top two-year-old filly in 1973 and top three-year-old filly in 1974. “She was known for being a speed horse. So, when the gates opened, everyone knew we’d be going to the lead. The question everyone had, including myself, was, “Will she be able to go two turns?” Her trainer, John Morahan, did an excellent job getting her ready. He ran her up and down hills at his farm, and had her legged up and ready to go. It was one of my most memorable wins.”

While Hawley’s string of victories in the stake would come to an end the next year (Reasonable Win romped to a seven-length victory under Richard Grubb in 1975), he would go on to win the race three more times. His eight Oaks wins are the most by any rider.

It all started in 1970, when Hawley partnered South Ocean, a daughter of New Providence (the first horse to officially win the Canadian Triple Crown, in 1959), to start his remarkable run.

Bred by E.P. Taylor, who sent out a record 16 Oaks winners, South Ocean, who foaled 1977 Oaks victress Northernette, delivered a sterling performance, besting Fanfreluche, the highly regarded mutuel favourite.

“What a fantastic filly,” praised Hawley, of the multiple stakes winner, who finished in the top three in 17 of her 22 career starts. “She did everything you asked of her. She was very calm, cool and collected. As a jockey, you wish they all could be like this one. She was just a great horse.”

One year later, Hawley teamed with Lauries Dancer to win the Oaks. The daughter of Northern Dancer had a sensational three-year-old campaign, making her mark in both Canada and the U.S. (Delaware Oaks and Alabama Stakes). The bay was the unanimous pick as Canada’s champion three-year-old filly and took 18 of 22 votes in the Daily Racing Form’s poll for Canada’s Horse of the Year.

Bred by Angus Glen Farm of Unionville, ON, she was inducted into the Canadian Horse Racing Hall of Fame in 2006.

“She’s the best filly I’ve ever ridden,” Hawley said. “She would come from off the pace with this tremendous run. She would kick into another gear, and after that, she would find another gear, too. She was just awesome. We had great success together and I was lucky enough to be part of her amazing career.”

In 1972, the aptly named Happy Victory continued Hawley’s remarkable run in the Oaks.

Sent off as the favourite, the daughter of New Providence prevailed over a stubborn Harem Beauty to win by a half-length and deliver Hawley an Oaks’ natural hat trick.

“She was a very good filly,” recalled Hawley, of the Oaks favourite. “She had to work to get the win, but she dug in. I was hoping we’d get to the wire first, but in races like this, anything can happen. To her credit, she kept battling and wouldn’t let anyone get by her. That’s the way she was.”

Next year, it appeared the streak was in jeopardy. Not because of the horse – Square Angel – Hawley was riding, but rather, the formidable filly that stood in their way.

One glance at the final odds in the race chart spoke volumes: La Prevoyante was .05 to the dollar.

At 6-1, Square Angel, who foaled 1979 Oaks champion Kamar, was the second choice. At race’s end, she was first when it mattered most.

“She was certainly talented enough, but when you are going up against a horse like La Prevoyante, you ask yourself, “Can we do this? Can we beat her?” Well, on that day, Square Angel ran her eyeballs out and it was a brilliant effort,” Hawley said.

It was also a record-setting performance, one that stands to this day. The E.P. Taylor-bred miss stopped the teletimer in 1:48.4.

“I didn’t even know it was a record for the race, but that makes it even more special.”

There would be no sixth straight trip to the winner’s circle in 1975. Hawley was riding in California and didn’t have a mount in the race.

And while the streak came to an end, Oaks success wasn’t over for Hawley.

Five years after his triumph with Trudie Tudor, he would guide Kamar to victory. In 1988, he teamed with Sam-Son Farm’s Tilt My Halo (Canada’s top three-year-old filly) for win No. 7. Tiffany’s Secret, also a Sam-Son silk-bearer, delivered Hawley his final triumph in the Oaks.

“To win one Oaks is very special,” said Hawley. “To be fortunate enough to win five (straight), all with great fillies, really makes me feel lucky and proud. They were all at the top of their game the day they won.”

So, too, was the man in the saddle, a rider that will always be known for being mighty in the Oaks.