By J.N. Campbell
All the pretty filly needed was a folding lawn chair and some ice-cold lemonade to make it made in the shade.
The aptly named Sippin Pretty (Yaupon–Tiz Imaginary, by Tizway) was overlooked on the tote at 26-1, but those that did make a wager on the 3-year-old were rewarded handsomely as she flew home a winner in the GIII Victory Ride Stakes at Saratoga Race Course on Friday afternoon.
One of two trainees for Ian Wilkes in the feature, Sippin Pretty broke her maiden by 3 3/4 lengths in what was her second career race going six furlongs over the Gulfstream Park main track Mar. 5. The dark bay then shipped to Keeneland where she was tabbed as the favorite in an optional claimer Apr. 4. The result was a solid 5 3/4-length score. Ready for her first shot at stakes company, Sippin Pretty endured a tough trip in the GII 8 Belles Stakes at Churchill Downs May 1 and finished sixth.
The daughter of Yaupon, who took over a two-month break, returned to the races at big price here. Sippin Pretty broke alertly and came through along the rail to run fourth as Iron Orchard (Authentic) showed the way up the backstretch. Following the three-wide move of favorite Goodall (Yaupon) around the far turn, the 26-1 shot angled outside for the drive home.
Goodall looked to be in control heading for the eighth pole, but Sippin Pretty was just beginning to find her best stride. The 3-year-old collared her target by the sixteenth marker and strolled home to upset the applecart.
Goodall was the runner-up, while 5-2 second choice and 'TDN Rising Star, presented by Hagyard,' Tommy Jo (Into Mischief) finished 10th.
The other Wilkes trainee at odds of 19-1, Fine Chardonnay (Maclean's Music), acquitted herself well in third.
Trainer Ian Wilkes said he told jockey Ricardo Santana before the Victory Ride, “Break good and then ride the race. The only thing I asked him was to break good. If she was on the lead, that's fine–if she's sitting second or third–I wanted her in the race, that's her style. She's naturally quick.
“I loved her that day [in the Eight Belles] and really thought she'd run big, but she broke bad and just wasn't herself that day. She made a run at the end of that race, but just wasn't herself. So, I freshened her up with the idea to run her in here with the Test Stakes down the road.”
Randy Bloch with jockey Ricardo Santana Jr. | Sarah Andrew
“We are pretty stoked and pretty excited,” said co-owner Randy Bloch. “I was just screaming, saying 'let's go!' She did fire today and we're really excited.
“Ian [Wilkes] picked her out at the sale,” he said. “Ian is family and we've been training with him for almost 25 years.”
On a potential next start in the $500,000 GI Test Stakes Aug. 8, Bloch said, “We hope so. Assuming she comes out of this in good shape, absolutely.”
Pedigree Notes:
The sophomore sire Yaupon (by Uncle Mo) now has his third graded winner to go alongside Albus and Booked.
The winner's dam is responsible unraced 2-year-old filly in-training First Cowgirl (Bolt d'Oro) and a yearling filly by Two Phil's. Tiz Imaginary foaled a filly by Maximus Mischief Apr. 18.
Sippin Pretty is part of an extended female family which includes champion 3-year-old filly and GI Frizette Stakes heroine Surfside (Seattle Slew).
VICTORY RIDE S.-GIII, $225,000, Saratoga, 7-10, 3yo, f, 6 1/2f, 1:17.59, ft.
1–SIPPIN PRETTY, 120, f, 3, by Yaupon
1st Dam: Tiz Imaginary (MSW, $281,877), by Tizway
2nd Dam: Imaginary Gold, by Mr. Prospector
3rd Dam: Starlet Storm, by Storm Bird
1ST BLACK TYPE WIN, 1ST GRADED STAKES WIN. ($150,000 Ylg '24 KEEJAN; $190,000 RNA Ylg '24 KEESEP; $75,000 Ylg '24 FTKOCT). O-Bloch, Randall L., Six Column Stables LLC, Davis, Mike and Rice, Gene E.; B-Clarkland Farm LLC (KY); T-Ian R. Wilkes; J-Ricardo Santana, Jr. $123,750. Lifetime Record: 5-3-1-0, $257,190. *1/2 to Mr Bob (Practical Joke), SP, $221,204. Werk Nick Rating: A. Click for the eNicks report & 5-cross pedigree. Click for the free Equineline.com catalogue-style pedigree.
2–Goodall, 122, f, 3, Yaupon–Moon Over Mag Bay, by Malibu Moon. 1ST GRADED BLACK TYPE. ($62,000 Ylg '24 FTKJUL; $525,000 2yo '25 OBSAPR). O-Spendthrift Farm LLC; B-Mark Allen Toothaker, William Heiligbrodt & Corrine Heiligbrodt (KY); T-Steven M. Asmussen. $45,000.
3–A Fine Chardonnay, 124, f, 3, Maclean's Music–Andele, by Bernardini. ($20,000 Ylg '24 FTKOCT; $85,000 2yo '25 EASMAY). O-Philip Griesinger; B-Alpha Delta Stables, LLC (KY); T-Ian R. Wilkes. $27,000.
Margins: 1 1/4, 3 1/4, 2 3/4. Odds: 26.59, 2.07, 19.13.
Also Ran: Sneaky Good, Carmel Coast, Peach Tie, Tessellate, Mythical, Iron Orchard, Tommy Jo.
Click for the Equibase.com chart or the TJCIS.com PPs. VIDEO, sponsored by FanDuel TV.
SIPPIN PRETTY serves up a 26-1 upset for her first stakes victory in the Grade 3 Victory Ride Stakes under @RSantana_Jr for trainer @IanWilkesRacing. pic.twitter.com/kUlfTGaFYb
— NYRA (🎪) (@TheNYRA) July 10, 2026
Not a subscriber? Click here to sign up for the daily PDF or alerts.
