Highclass Harry, trained by Illowa trainer Maureen Dwyer and ridden by her granddaughter Melissa Julius, defeated hot favourite Zoupremo and Don't Matter in the 1400-metre race.

Maureen's husband Leo retired after 58 years as the Warrnambool clerk-of-course at the Woodford meeting on Tuesday.

"It's been a huge couple of days for the family," she said.

"The win of Highclass Harry is a wonderful result but the best thing is he was ridden by Melissa and our son Eddie, who is a clerk-of-course at Terang, led her back into the winners' stall.

"We could not have scripted the last two days any better.

"Melissa has only had a handful of rides back after a break from the saddle, so for her to win a race on a horse we train is extra special.

"We're all pretty excited with the result."

Maureen, who trained Follow The Band to run second behind Thackeray in the 1979 Warrnambool Grand Annual Steeplechase, had her last winner back in August 2013.

"I've only had a handful of runners in the last six years," she said.

"Shiny Manners was my last winner when he won a high-weight race at Warrnambool."

Highclass Harry was the first leg of a double for Julius.

She rode the Daniel Bowman-trained Favonski to win the time-honoured Peter Blank Sprint for the Warrnambool trainer.

Leo bowed out of his role as Warrnambool clerk-of-course at the Woodford Cup meeting on New Year's Eve.

The 82-year-old held the role for 58 years.

The father-of-seven, who has fond memories of watching champion jockeys, horses and trainers winning races over almost six decades at Warrnambool, told The Standard at the course that time had caught up with him.

"I've had a great run and loved every minute of it," he said of his long, respected career.

"I would not change a thing. The time is right for me to retire."

Have you signed up to The Standard's daily newsletter and breaking news emails? You can register below and make sure you are up to date with everything that's happening in the south-west.