In the seven-furlong event, the earner of $966,160 will face four rivals, including salty four-year-olds Dancer's Bajan and Yummy With Butter, and six-year-old stalwart Archers Alyancer, who will be the first Woodbine stakes mount for apprentice Melanie Pinto.
Owned by Charles Fipke, Not Bourbon hasn't raced since finishing sixth in the Prince of Wales Stakes at Fort Erie on July 13.
"He's tucked a leg on the wall or something. He's sound. But I can't run him," explained trainer Roger Attfield after learning of the incident.
The minor injury wasn't the first setback of the colt's three-year-old campaign.
The five-time winner entrapped his palate during the running of the 1 3/16 mile Prince of Wales, which is the second jewel in Canada's Triple Crown of Racing.
"It's a distressing thing for a horse to have his oxygen cut off. We did a myectomy (throat surgery) on him. He didn't miss any time, but we backed right off on him," explained Attfield.
Not Bourbon, who will be piloted by Jono Jones, worked a half-mile on September 13 over Polytrack in :46 4/5, breezing. The bullet move was best of 65 workers at the four-furlong distance.
The chestnut son of Not Impossible, who is a full brother to retired turf sensation Perfect Soul, seeks his fourth stakes score of the season. In addition to winning the Plate by a head, he also won the Queenston and Plate Trial Stakes.
A victory in the Overskate, which is slated for race six on Saturday's 10-race programme, would push Not Bourbon's career earnings over the $1 million plateau.
OVERSKATE STAKES
POST - HORSE - JOCKEY - TRAINER
1 - Archers Alyancer - Melanie Pinto - John Simms
2 - Not Bourbon - Jono Jones - Roger Attfield
3 - Dancer's Bajan - Corey Fraser - Robert Tiller
4 - Grazettes Landing - Patrick Husbands - Mark Casse
5 - Yummy With Butter - Emma-Jayne Wilson - Mark Fournier