They are the memories that the Webb and Tilley family will be able to cherish forever.

Apprentice hoop Olivia Webb is on the comeback trail after giving birth to her first son Jaggar just over four months ago and has hit the ground running in recent weeks.

The 25-year-old has piloted seven winners since returning to race riding early last month. 

She ticked off another milestone on Friday at Caloundra as young Jaggar was at the races to see his mother ride a winner for the first time. 

Webb did so when she scored aboard Thelwell for popular Deagon horsewoman Sharryn Livingstone in the Class 5 Handicap over 1000 metres.

Not long after Webb went past the winning post, young Jaggar was in the mounting yard for some memorable photos.

The up-and-coming hoop was rushed into hospital at the 36-week mark of her pregnancy before she welcomed him into the world.

Jaggar had been at the races a few times before Friday's triumph and the young jockey says it is a special moment the family will be able to cherish forever. 

"He doesn't get to the track too often, usually he will go with my partner Ross on a Saturday because I obviously can't have him during the races and be watching him," Webb said.

"It was pretty cool for him to be there on Friday and watch me ride a winner.

"He won't remember it now but in a couple of years he will be able to turnaround and look back at those photos.

"It is what those photos will mean to me in a couple of years."

Webb's partner Ross Tilley is the brother of Queensland hoop Les Tilley. 

The family have recently relocated to the Sunshine Coast area from Toowoomba to be closer to Webb's parents for more support in the early stages of their son's life. 

Webb has been riding since the 2020-21 campaign and has had her battles with weight over the years. 

But, since her pregnancy, she says it has been smooth sailing. 

The apprentice jockey believes it is the fittest she has ever felt in her career.

"I feel really good since I have come back, the ball has got rolling really quickly and consistently for me," she said.

"I have never honestly felt so strong at the races as well as being in touch with the horses, which was has been really good.

"Before I had Jaggar, I was really struggling to ride at 53-54kg and now, I am walking around at 50kg or just over.

"My body has flourished since having him, I am strong and I am not fighting with my weight as I am eating really well.

"It has been really good for me."

While it was a big day for Webb and her son on Friday, it was also a memorable occasion for trainer Livingstone as she prepared a winning double. 

Thelwell's victory was paired with Click Click Boom scoring in a Benchmark 68 Handicap for the three-year-olds. 

As Livingstone just has the four in work, it was a significant achievement for her to salute with half of her team on one program. 

"It was good to put Olivia on and see her ride a winner," Livingstone said.

The Livingstone team is not a stable Webb has done much riding for previously in her career and the young hoop says plenty of new doors have been opened since she returned to riding almost eight weeks ago. 

Thelwell certainly loves the northern trips from Deagon to Caloundra as he has now won on three occasions at the track. 

"I tracked the favourite in the race, I was three-wide with cover," Webb said.

"Sharryn just said he likes a tough run and he was travelling really well throughout.

"As soon as we came into the straight, I eased hm out and he just kept going and I was really happy with him."

Earlier this month, Webb rode a winner at a Gold Coast day meeting on a Saturday before heading to Clifford Park and claiming a triumph under lights, as well.