Horse trainer Barry Ratcliff is hopeful First Time Lucky will see him lift the Kempsey Cup for the first time in 18 attempts.

Meanwhile horse trainers Daniel and Rocky Simonetta have two chances at glory as Prima Stella and Mister Mcilroy will jump in the prestigious race.

Ratcliff has been pursuing the Kempsey Cup for almost two decades but has been forced to settle for a place on four occasions.

The lifelong horse trainer is hopeful this will be the year he gets the monkey off his back.

"It would be a lot of weight off my shoulders if I can get the win," Ratcliff told the Argus.

"To win my hometown Cup is important to me. It's not about the money, it's about the prestige of being able to say I won the Kempsey Cup."

First Time Lucky opened at $17 with the bookmakers but has been first past the post in its last two starts. The four-year-old gelding also has one win from as many runs at the Kempsey track.

Barry will have four horses from his 10 horse stable racing tomorrow.

The Simonetta's contenders have also been in good form.

Mister Mcilroy strung three wins in a row together before falling to eighth in its last start in Wyong, while Prima Stella earned a place in its second last run.

Daniel claims both horses are a chance of winning but admits it will be difficult given their barrier draw.

"They are both starting out wide which hurts a bit, especially on the Kempsey track," Daniel said.

"But Mister Mcilroy has had some tough barrier draws of late and has still managed to have those three wins in a row so we aren't writing him off.

"They are both ready to go though. They have been training really well and I can sense they are in for a big race."

Daniel and Rocky will be entering their first Kempsey Cup as partners, after they joined forces in September last year.

Rocky, who has valuable experience from training horses in Sydney, has made a big difference to the way the horses are put through their paces.

"Rocky has a lot of city experience, which is huge around here," Daniel said.

The Kempsey Cup is race seven and is scheduled to jump at 4.55pm.

The first race jumps at 1.15pm.

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