Jimmy The Bear’s first attempt over 2400 metres ended in narrow defeat, with the John Moloney-trained Dictionary prevailing in Saturday’s $175,000 VOBIS Gold Stayers at Caulfield. It was a breakthrough city win for the five-year-old, who hails from one of the most famous families in Australian racing.

Dictionary is out of Collins, a daughter of Desert King and Tugela, which makes her a sister to the legendary Makybe Diva. The gelding is by All Too Hard, the half-brother of Black Caviar, giving him links to two of Australia’s greatest mares. “He’s got that Makybe Diva connection and he’s also got Black Caviar on the other side, through All Too Hard, so he’s got a double whammy of the best mares around,” an excited Moloney said.

Patiently ridden by Daniel Stackhouse, Dictionary ($14) surged along the fence to nab the $1.40 favourite Jimmy The Bear in the final strides, winning by half a head. Midnight Glow ($12) finished 2-3/4 lengths away in third.

It was the sixth win for Dictionary, who had finished third in last year’s edition of the VOBIS Gold Stayers. Saturday’s success took his earnings to $312,530, including bonuses, after 37 career starts. The gelding, a $110,000 Magic Millions purchase, has been a slow maturer but continues to improve with racing.

“Each time I’ve run him at a trip he’s been able to step up and do something, so he’s been good like that,” Moloney said. “Realistically, I didn’t think I could beat him (Jimmy The Bear), but he just got a beautiful run, he got the right sit and he was able to take him out at the finish.”

Punters interested in future races for Dictionary or Jimmy The Bear can find markets at leading betting sites.