by Steve Bailey

The last time Kip Deville did not land in the winner’s circle, he finished second by just a length to Shakespeare in the 2007 Woodbine Mile Stakes (Can-G1).

The five-year-old Kipling horse will take a second shot at the $1-million turf test on Saturday as he takes on seven challengers, including fellow Grade 1 winner Ventura, at the Toronto, Ontario track.

For the first time, the race is part of the Breeders’ Cup Challenge “Win and You’re In” series, with a berth in the Breeders’ Cup Mile (G1) on October 25 at Santa Anita Park awaiting the winner.

Trained by Richard Dutrow Jr., Kip Deville rebounded from his Woodbine Mile defeat to capture the NetJets Breeders’ Cup Mile by one length over Excellent Art.

Kip Deville has been perfect in two starts this season, taking the Maker’s Mark Mile Stakes (G1) on April 11 at Keeneland Race Course and the Poker Handicap (G3) after a three-month layoff on July 13 at Belmont Park.

Now, following another lengthy vacation, he returns to Woodbine to prep for a possible repeat victory in the Mile.

"He's been doing great since [the Woodbine Mile] last year," Dutrow said. "He's just been in a zone of his own. He's incredible. He's doing unbelievable. I'm just really excited about being able to watch him run again. He certainly appears to be (a better horse than last year). He's just so much more confident in himself.  He's matured into that type of a horse.

"The way he is now, we kind of just let him fall into the race the way he wants to because he knows what to do and when to do it. If he finds himself on the lead, that's fine with us."

Kip Deville, who will break from post four under jockey Cornelio Velasquez, was installed as the 6-to-5 morning-line favorite for the race, which has only been won by the favorite three times: Soaring Free in 2004, Leroidesanimaux in ‘05 and Shakespeare last year.

Conditioned by Racing Hall of Fame trainer Bobby Frankel, Juddmonte Farms' homebred Ventura was named the 4-to-1 second choice on the morning line as she tries to become the first filly to capture the Woodbine Mile.

The four-year-old Chester House, filly enters the race off a nose loss to Diamond Diva in the $750,000 CashCall Mile Invitational Stakes (G1) on July 5 at Hollywood Park. She has won three of five starts this year, including the Just A Game Stakes (G1) on June 7 at Belmont Park.

A win would give Frankel his third Woodbine Mile victory, following Riviera in 2000 and Leroidesanimaux in ’05.

"I've had five Eclipse Award-winning fillies, but I'd rate her [Ventura] pretty good,” Frankel said. “We'll see how she does in this race [before planning her next start]," said Frankel. “But we're looking for a little pace in the race." 

Tucci Stables’ Just Rushing is one of six locally based horses that will try to upset the favored invaders.

The seven-year-old Wild Rush gelding enters off a 1 ¼-length victory in the Play the King Stakes (Can-G2) on August 23 at Woodbine. Jockey Jim McAleney, who was aboard in the Play the Game, will retain the mount and break from post three at morning-line odds of 5-to-1.

"It's a good draw; number three, close to the rail," trainer Sid Attard said. "It looks like he's the only speed, so we'll see."

Two other turf stakes—the $750,000 Northern Dancer Stakes Presented by V-Tech (Can-G1) and the $300,000 Canadian Stakes (Can-G2) also will be run on the card.

Steve Bailey is deputy news editor of Thoroughbred Times

The field, in post-position order, including (sire), jockey, weight, and trainer:

1. Mulmur (Smart Strike), Eurico Da Silva, 117, Mark Frostad;

2. Rahy's Attorney (Crown Attorney), Slade Callaghan, 119, Ian Black;

3. Just Rushing (Wild Rush), James McAleney, 121, Sid Attard;

4. Kip Deville (Kipling), Cornelio Velasquez, 124, Richard Dutrow Jr.;

5. Wollemi Pine (Aljabr), Emma-Jayne Wilson, 117, Ian Black;

6. Ice Bear (Maria's Mon), Chantal Sutherland, 117, MacDonald Benson;

7. Palladio (Lycius), Richard Dos Ramos, 117, Roger Attfield; and

8. Ventura (Chester House), Garrett Gomez, 124, Bobby Frankel.