Inside Track for September 20-21

A look at some of the top highlights from the past weekend of racing at Woodbine.

Upset alert

Cool Kiss tracked down her first stakes win in style Saturday at Woodbine, surging late to claim the $150,000 Durham Cup (G3) at 17-1.

Squaring off with the likes of multiple graded stakes winner Paramount Prince (4-1) and last year’s Durham Cup champion Dresden Row (even-money), Cool Kiss remained poised and patient en route to the stunning comeback victory.

A $40,000 claim by trainer Martin Drexler on behalf of owners Stephen Chesney and Cory Hoffman, the Kantharos dark bay is now 4-4-1 from 23 starts.

Bred in Ontario by Phoenix Racing, Cool Kiss paid $36.90.

Put a bow on it

Piper’s Gift was on full display in Saturday’s sixth at Woodbine.

Slotted into post six in her first test after a fifth in last month’s Catch A Glimpse Stakes, the rookie Dale Desruisseaux trainee confidently stalked the pace before unleashing a rapid kick to capture the 6-furlong sprint by eight lengths.

The impressive showing resulted in Piper’s Gift’s first career trip to the winner’s circle from three tries.

Bred and owned by Chiefswood Stables Limited, the emergent bay filly, at 5-2, paid $7.20.

Little Teddy goes big time

A mighty effort from Little Teddy in Sunday afternoon’s $100,000 Zadracarta Stakes earned the veteran roan her second career stakes triumph (2024 Georgian Bay).

After recording consecutive runner-up finishes in the Algoma and Ballade, both also at Woodbine, the 4-year-old daughter of Frac Daddy–Explosive Leah got over the hump with a 5 1/2-length score under a strong ride from jockey Austin Adams, who earned his first stakes badge.

Purchased for $11,457 at the 2022 Canadian Premier Yearling Sale, Little Teddy has made nearly $320,000 across 14 lifetime starts (6-4-2).

At 5-2 on Sunday, the Santino Di Paola charge paid $7.60.

Stay tuned

Live racing continues Thursday. First post is 5:30 p.m. ET.