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Highland Jakk has registered his maiden city win following four victories on country tracks.

A horse trainer Robert Hickmott once considered a Caulfield Cup hope has broken through for his maiden city win with a narrow victory at Moonee Valley.

Highland Jakk took out the Ladbrokes Same Race Multi Handicap (2040m) on Saturday to go with his four previous wins on country tracks. 

Ridden by Craig Williams, Highland Jakk ($9) scored a long head win over Fighting Arrow ($12) with Uniquely ($20) a further three lengths away third. 

Back in his three-year-old days, Highland Jack finished third behind Pancho and Russian Camelot in a Listed race over 1800m during Melbourne Cup week which convinced Hickmott of the now six-year-old's future as a stayer. 

But a bleeding attack in his following preparation put an end to those Caulfield Cup dreams and the furthest trip Highland Jakk had raced at prior to Saturday's win was 2015m when successful in maiden grade at Seymour. 

"He ran third to Pancho and Russian Camelot in a good three-year-old race at Flemington during the Carnival and then he bled at his next campaign," Hickmott said. 

"That took the wind out of him. I thought he might have been a Caulfield Cup horse until that bleed. 

"He was only a $10,000 horse, but he's been a terrific horse for the owners, so hopefully we can go through the grades and win a few more." 

Highland Jakk has now won five of his 28 starts and more than $230,000 in prize money after Saturday's benchmark 70 grade win and Hickmott said it was now the time to try the son of Melbourne Cup placegetter Jakkalberry at 2400m. 

"The natural progression is to a benchmark 78 and at a mile-and-a-half and there is one next week, but it might be a bit soon," Hickmott said. 

"But I'm looking forward to getting him up to a mile-and-a-half and giving him a crack."