Olive has started more than 15 horses in the prestigious race and has gone close with a few placings, but winning the prestigious race has so far eluded him.

The Canberra trainer has won a list of feature races - a Wagga Cup, two Gundagai Cups and group one races with his mighty mare Single Gaze - but it's the XXXX Snake Gully Cup (1400m) that holds the greatest appeal.

The multiple premiership winning trainer has another opportunity on Friday with early favourite Ready To Humble ($3.60 NSW TAB) and reigning Gundagai Cup winner Maid Of Ore ($13).

"I have been trying and trying to win it and I think I have finished second three times," Olive said.

"I have an attachment to the town and the Snake Gully Cup meeting is one of my favourite race days.

"Obviously Single Gaze was part part-owned in Gundagai, but my apprentice jockey Billy Owen also comes from there, I sponsor the Gundagai Tigers and some of my best mates are from the town.

"It's one of those races I really want to win."

Olive has started favourites in the $100,000 feature in the past but come up short and he loos to have two terrific chances again despite the strength of the opposition.

Maid Of Ore hasn't raced for 18 weeks and is coming off a last start fifth in the Grafton Cup, while she also ran fifth in the Wagga Cup and fourth in the Ipswich Cup.

Olive liked the way Maid Of Ore trialed when second at Canberra recently and feels she can acquit herself well despite a wide alley and a big weight of 59 kilograms.

"Obviously the distance is short of her best and 1400 metres at Gundagai is a bit different for her first-up, but I can't fault how she is going," he said.

"She is a quality mare who keeps getting better and if she can be somewhere near them she will be finishing off very strongly."

Ready To Humble has only raced twice since Olive took over his training for a third in the Coonamble Cup and second in the Cootamundra Cup.

"I gave him a week in the paddock after Cootamundra where he was beaten fair and square," he said.

"He will race on the pace and loves it wet so he has a few things in his favour."

The galloper drops three kilograms on his last start and is proven on a heavy surface with a win and a third from two starts.

The weather forecast for rain on Thursday night and more to follow on Friday and Saturday has everyone guessing about the future of the two-day carnival.

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Gundagai trainer David Blundell will start Thistledo ($21) in the Snake Gully Cup and hopes the veteran can deliver him a second feature.

Blundell knows better than most how the Gundagai track will play if there is too much rain and hopes for the sake of the meeting that the forecast is off the mark.

"It all depends on how much rain we get on the day because the surface is pretty good it's just when we get the rain and how much," he said.

As for his own chances in the Cup, Blundell is looking at the race from a different perspective this year.

"I couldn't be happier with how he has worked and he is 100 per cent now," he said.

Blundell has had to rely on fellow trainer Jim Scobie, his daughter Michelle and others to look after his team following recent surgery which kept him hospitalised and also at home.

He is unlikely to attend the races but will keep close tabs on Thistledo and his other starters.

"He ran very fast time for his last 600 metres in his fast work and I think he will run a big race," Blundell said.

One of the best performed runners in the Cup is Nictock who, if he starts, will be racing for the second time in six days.

The gelding led when a gallant third at Rosehill last Saturday behind Blaze A Trail over 1200 metres.

Nictock won seven of his first eight starts in 2017 and is at his peak after four runs back from a spell for trainer Marc Conners.

Peyton Place, which will carry the number one saddle cloth, is proven in the wet and will be the first ride in the feature for apprentice jockey Molly Bourke.

The young apprentice has been out of action with a thumb injury and Gundagai will be her first meeting back for several weeks.

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