Abdullah Saeed Almaddah's Mizzen Mast gelding was guided to his second graded stakes win by jockey Javier Castellano and finished the six furlongs in 1:08.23 over the firm turf.
“He is a very straightforward horse and he’s learning every single race,” Castellano said.
Co-second choice Commute took the lead out of the gate and lead the field through the first half-mile, running through fractions of :22.7 and :45.26. Don Camillo stalked closely in second as Noholdingback Bear and longshot Sweet Grass Creek raced a length back in third and fourth. The Brad Cox-trained Green Mask traveled unhurried in fifth along the rail.
Out of the turn, as Commute held a half-length advantage, Castellano angled Green Mask off the rail and looked for running room in the stretch. Finding a path between tiring Don Camillo and Noholdingback Bear, Green Mask was turned loose and easily chased down Commute in the final furlong under a hand ride. Calgary Cat, closing from last in the field of seven, was flying on the outside but was no match for the winner and finished second two lengths behind.
Commute held for third with Commend in fourth. Noholdingback Bear, Don Camillo, and Sweet Grass Creek completed the order of finish.
Off at odds of 3-5, the winner returned $3.20, $2.40, and $2.10.
For the first time this year, the Highlander is a Breeders' Cup Challenge "Win and You're In" race for an automatic berth in the Breeders' Cup Turf Sprint (G1T) Nov. 4 at Del Mar. Green Mask was fifth in last year's edition of the Turf Sprint and third in 2015.
"A big reason for coming was the 'Win and You're In' program," said Cox, who registered his first win at Woodbine. "It worked out well. There was a little concern with running him back in 22 days but he breezed Monday at Belmont. He had a great breeze, came out of it in good order so we thought we would give him a shot."
Bred by D. J. Stable out of the Forestry mare Bonsai Beauty, Green Mask has finished first or second in his last six starts, going back to the Bonapaw Stakes in December at Fair Grounds Race Course & Slots. In that time period, the 7-year-old won the five-furlong Twin Spires Turf Sprint Stakes Presented by TwinSpires.com (G3T) by two lengths and was narrowly denied in both the grade 2 Shakertown Stakes and the grade 3 Jaipur Invitational Stakes. He now boasts a record of 7-8-3 from 26 starts, with earnings of $914,761.