The pair have met on five occasions, with the tally locked at two wins apiece.
Showemhowitsdone won both the Listed Gore Guineas (1335m) and Listed Dunedin Guineas (1500m), while The Gift took top honours in the Haase Marshall Drainage Premier (1400m) and Listed NZB Insurance Stakes (1400m).
The Gift was freshened after her last start win in the NZB Insurance Stakes and trainer Robert Dennis said she has returned a more relaxed filly.
"She is relaxing a little bit better in her work now, she used to be all gung-ho and wanted to get on with it," he said.
"After her last start she had a week out in the paddock and had four weeks work leading up to this race."
While Dennis is looking forward to tackling Showemhowitsdone once again, he said there are also a number of other dangers in the race.
"Showemhowitsdone is there, they have met each other four or five times, but there are other horses in the race as well. There is plenty of competition there," he said.
"I have got a good jockey in Jacob Lowry and I trust him to ride a good race."
Stablemate Ocean Point will also contest the race, having followed a near identical path to The Gift.
"She has followed pretty much the exact same path as The Gift," Dennis said. "She had a week break and four weeks of work leading into it. She seems more or less her usual self, so hopefully we get another good run out of her."
Dennis was relieved to get a stakes placing with the daughter of Ocean Park in the NZB Insurace Stakes last start, as she had been knocking on the door for some time.
"She definitely deserved her stakes placing," he said. "She was robbed of one at Gore when Showemhowitsdone was a bit wayward late.
"She had two listed fourths before that and I wouldn't be surprised if she added to it this weekend."
A return to Riccarton in a fortnight to contest the Listed New Zealand Bloodstock Warstep Stakes (2000m) could be on the cards for both fillies if they perform up to expectations this weekend.
"The Warstep is two weeks later, so all going well they will head there," Dennis said. "But they would have to go good races to go again, but we will get Saturday out of the way first."
It's a long trek from Dennis' Southland base to Riccarton, however, the travel bodes no concerns for the Woodlands horseman who has made the trip several times this season.
"I have done it a few times now," he said. "This will be the eighth or ninth trip up to Canterbury this season. We have got a pretty good routine going and I have had good success at Riccarton lately.
"We head up tomorrow (Friday) and the horses know the drill, they know the place pretty well, so they settle in pretty good and usually eat up."It's not too much of a headache."