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Robert Shepherd celebrated a personal milestone with a win aboard Order By Commander in the Preferred 3 Trot at Grand River Raceway.

The 35-year-old Cambridge, Ont. resident entered the card with seven drives and two wins shy of 2,500 wins lifetime.

Shepherd’s first win of the night came early in Race two with Donald Lindsey’s three-year-old pacer Upland. However, the trip he was looking for came when Shepherd teamed up with Craig Yates’ trotter Order By Commander in Race 5 to make his milestone trip to the winner’s circle.

Order By Commander got away sixth and took cover behind Dragin The Wagon at the half to advance through the field. Shepherd went three-wide at the three-quarter pole and pulled away to secure a commanding four- length victory.

It was a pleasant surprise when Shepherd was presented with the milestone sign. “I knew I was close, but I thought I still had a few to go,” Shepherd laughed in a post-race interview. The win was the trotter’s second consecutive score, stopping the clock at 1:58.

Robert Shepherd’s first career win came in 1999 at the age of 19 at Charlottetown Driving Park in his native PEI with Whattheblazes, a chestnut pacer trained by his father Harold.

Ten years later in 2009, he hit his 1000th win with Secret Lives at Georgian Down. He notched 2,000 wins at Grand River Raceway in September 2013.

“I’d say my most memorable win was with The Bruster in the 2004 Nat Christie,” he recalled. Then 24, the $120,000 race at Stampede Park was Shepherd’s first major stake win, and came just two years after relocating to the west. He relocated to Ontario a few years later and quickly established himself as one of the province’s top reinsmen.

Shepherd is closing in on $18 million in career purse earnings.