The 50-year-old hoop has been riding winners at tracks in country NSW, Sydney, Canberra, Alice Springs, Queensland, South Australia, Victoria and even a small island off the coast of South Africa during a glittering 34 year career.

In that time he’s had more than 16,000 rides and notched close to 2,000 winners, including a Black Opal Stakes, Alice Springs Cup, three Wellington Boots and countless country cups.

He’ll be inducted into Cowra’s Sporting Hall of Fame on Friday night.

“Cowra, for a little town, really produces a lot of good sportspeople. To be put in the same class as the guys on the wall of the Hall of Fame is a great honour. It’s a big thrill,” Mathew said.

Born and raised in Wellington, Cahill spent childhood years living in Bathurst and Yeoval before the family settled in Cowra in 1984 when he was 12.

He began a jockey’s apprenticeship as a 16-year-old assigned to his father Ossie, and had his first ride on a horse called Papago in 1988.

Developing faster than others under the tutelage of his father and older brother Michael, Cahill quickly notched his first on Lucky Bally trained by his father.

Cahill quickly outrode his claim in the bush and took an opportunity in the city to ride for Rosehill trainer Jack Denham for six months.

“It was a good experience and a great education. I’d been at home all my life up until then, so that was a great experience. I did get a bit home sick but it was a big learning curve,” he said.

He returned to Cowra and completed his apprenticeship with his father at the age of 21. Five years later he moved to Canberra and established himself as one of the best jockeys in the nation’s capital.

Linking with the likes of leading Canberra trainer John Morrisey and Peter Staunton, Cahill rode winner after winner and picked up a couple of Canberra jockey premierships along the way.

In 1998 he rode Morrisey’s Speed Week to victory in the Group 2 Black Opal Stakes at Canberra’s Thoroughbred Park. The win remains one of Cahill's most memorable moments in the saddle.

“It was very special, I’d just moved to Canberra. It’s their major race of the year and a race I’d always wanted to win,” he said.

He lived in Canberra for about three years and then moved back to Cowra but continues to ride regularly in the nation’s capital.

Overseas, Cahill’s only ridden in Mauritius, a small island off the coast of Madagascar, located near the south-east coast of Africa. He went there in 2008 for two seasons.

“They race eight months of the year from May through to November and shut down for hot weather. They get big crowds, good atmospheres. Jockeys are contracted to a stable, I probably had about 16 wins each year. It was a good experience,” he said.

Since then he’s remained based in Cowra.

Almost every country cup has been crossed off Cahill’s list and he’s a six-time Cowra Cup winner. He’s won numerous Cootamundra, Bathurst, Albury, Parkes, Orange, Dubbo and Scone Cups. He’s also won the Wagga Gold Cup and Coonamble Cup.

“I’m not sure on the numbers,” Cahill said.

He’s ventured to the city over the years and has struck some luck, most recently in the Group 3 Summer Cup on leading trainer Chris Waller’s gelding Montauk on Boxing Day in 2017.

“You don’t get a lot of opportunities being out here. You need to be based in Sydney to get good opportunities. I’ve always liked the country lifestyle. I’ve been down there a bit over the years and had some luck. Probably one of my best seasons I rode seven or eight down there which is quite good for a country jockey,” he said.

Cahill identified horses Siddenhausen, He’s A Prince, Miss Comanche and Foxbrook as the best country horses he has ridden.

He’s A Prince race to victory in a Canberra Guineas, Miss Comanche took out a Wagga Plate and Foxbrook was owned by his mother Margaret and trained by his father Ossie.

Siddenhausen won seven in a row to start his career.

He has lined up against some of the best bush jockeys going around including the likes of Bill Aspros from Bathurst, Wayne Weate from Walgett, Wagga’s Graham Power and from the southern districts Garry Buchanan. When he was an up-and-comer, Cahill raced against multiple premiership winning jockey from the central district Dennis Firth. 

“He was a legend,” Cahill said.

These days, Cahill says there’s none better than Greg Ryan.

“Greg Ryan is probably as good as I’ve seen.”

While the Black Opal’s at the top of his list, Cahill identifies his three Wellington Boot victories in the past five years as special triumphs.

The biggest race on the town’s calendar – the town he grew up in and a town his father trained horses in for two decades. It was a race that evaded Cahill for years, he explained.

“I think I had 13 or 14 rides in it and never ran a place, my luck changed.” 

Cahill says the industry has changed a lot over the years. 

Track surfaces are better, rails are now plastic rather than steel or aluminium, barriers are better and prizemoney in the bush has improved significantly, he said.

“I started when I was 16. I got $35 for my first ride, prizemoney then was $700 to the winner. I’ve never seen country racing better as far as money goes. It’s $11,000-to-the-winner now, mind you that’s 34 years ago,” Cahill said.

Winning is the obvious answer to what’s the most satisfying aspect of being a jockey, but Cahill gets a big kick out of helping educate a young horse and witnessing them progress through the classes.

It’s something he said he hasn’t done a lot of lately because of the little amount of track work he rides.

“You ride the horse in work and educate them and they win three or four races and progresses it’s really satisfying,” he said.

When asked what the worst part of the job is, Cahill was quick to highlight the amount of travelling involved during a regular week, and the strict diet he has to maintain. 

“Sometimes I might do 1500km or 1000km a week. It has to be done there’s no way around it. That’s probably the worst part of the job, that and having to diet.”

He said he owes a lot to his father Ossie and his older brother Michael, 53.

Cahill says he’ll continue riding for as long as he thinks he’s racing “competently”. 

“I didn’t think I’d ride this long, it’s a young guys game. I’ve always enjoyed what I’ve done. I would have liked to have risen to greater heights but I’m happy I made a living out of the business.

“I’m lucky I haven’t been hurt badly. I just like riding well and riding winners and trying to do the job competently.

“Once I stop riding I’m not sure where I’m going to place myself.”

Cahill is a two-time winner of the Cowra Sportsperson of the Year, and joins his brother Michael Cahill in Cowra’s sporting Hall of Fame. “It’s nice to get there alongside him,” he said.