Jumps newcomer Montgomery is stepping up in grade in Wednesday's Australian Hurdle in an attempt to repeat his eight-length win when he made his debut over obstacles.
The Cindy Alderson-trained gelding has earned a feature-race entry after his devastating first attempt at jumping but Alderson is under no illusions the eight-year-old will find it another cakewalk.
Montgomery will meet Westsouthwest, the horse he thrashed at Sandown on August 7, 7kg worse at the same track.
"We're greatly disadvantaged at weights compared to last time but the horse has thrived since he last raced," Alderson said.
"Hopefully, he can take that form into this race but it's a step-up and there are some experienced jumpers there."
Westsouthwest's trainer Robert Smerdon is frank about his horse's chances saying that even with less weight it could be difficult to bridge the gap.
"I'm not sure if it's enough but it will bring them closer together," Smerdon said.
"Montgomery was super impressive and is probably on the up.
"My horse will be better at it once he comes back next season."
In the other feature race, the Australian Steeplechase (3900m), the Ciaron Maher-trained Bashboy will be looking to stretch his unbeaten record over jumps this season to five.
The reigning Australian Jumper of the Year has won all four steeplechase starts this campaign including the Grand National Steeplechase where he lugged 72.5kg over 4500m.
It will be equally punishing again at Sandown with the 10-year-old slugged with 74.5kg.
He will be giving 10kg to his nearest rival in the weights with premier jumps jockey Stephen Pateman aboard.
The Australian Steeplechase and the Australian Hurdle are the final two legs of this year's J J Houlahan Jumps Championship.
The horse and jockey titles have already been wrapped up by Bashboy and Pateman respectively, but the trainer's award will go down to the wire.
Smerdon goes into the meeting with a 92 points to 84 lead over Maher.