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1ST RACE—JUNIOR FLAT RACE–PONIES
The Raymond R. Ruppert Memorial
Small Pony
| Place | Horse | Rider | Trainer | Owner |
| 1 | Missy | Kellie Witte | Kellie Witte | Kellie Witte |
| 2 | Emmy-Lou | Gabby Bernier | Suzanne Stettinius | Mint Meadows Farm |
| 3 | Blueberry Muffin | Erin Swope | Erin Swope | Erin Swope |
| 4 | Coloring Lesson | Ross Mace | Fritz Boniface | Hunting Ground Farm |
| 5 | Cricket | Darby Hyde | Darby Hyde | Darby Hyde |
Medium Ponies
| Place | Horse | Rider | Trainer | Owner |
| 1 | Domino | Catie Keil | Catie Keil | Catie Keil |
| 2 | Splish Splash | Audra Campbell | Audra Campbell | Audra Campbell |
| 3 | My Little Drummer Boy | Paige Vallee | Paige Nicole Vallee | Paige Nicole Vallee |
| 4 | Cinnamon Twist | Katie Hindt | Stacy L. Hindt | Katie A. Hindt |
Large Ponies
| Place | Horse | Rider | Trainer | Owner |
| 1 | Bold Initiative | Lindsey Capps | Stacy L. Hindt | Katie A. Hindt |
| 2 | B's Little Magic | Quinn Scala | Suzanne Stettinius | Mint Meadows Farm |
| 3 | Jordan | Erin Swope | Erin Swope | Erin Swope |
| 4 | Glenmore Secret Romance | Eric Poretz | Eric Poretz | Eric Poretz |
| 5 | Coastal Ice | Scott Wolfendale | Marcus Assia | Ken Kaelin |
| Scr | Dude Please | Paige Vallee | Paige Nicole Vallee | Paige Nicole Vallee |
Second Race: The William H. Brooke Memorial Maiden Flat
| 1 | Celebratory | Diana Gillam | Jeremy Gillam | Jeremy Gillam |
| 2 | Music Tune | Jacob Roberts | Katherine N. McKenna | Katherine N. McKenna |
| 3 | Straightrazorblade | Tom Foley | Edward L. Graham | Mark Russack |
| 4 | Salt And Vinegar | Lilli Kurtinecz | Lilli Kurtinecz | Jodi Rauso & Lilli Kurtinecz |
| 5 | Mojave Moose | Jacob Roberts | Todd J. Wyatt | Peter A. Jay |
| 6 | Love Of Lite | Suzanne Stettinius | John E. Worsley | John E. Worsley |
| 7 | Complete Sport | Richard Boucher | Lilith Boucher | Lilith Boucher |
| 8 | Storm Cat Valay | Anthony Aguirre | Henry Villari | Greg Hutton |
| 9 | St Of Circumstance | Todd McKenna | Todd McKenna | Keystone Thoroughbreds |
| LR | Albertha The Cook | David Santos | Alexandra S. White | Cedarhurst |
| Scr | Uncle Nutty | James Slater | Brianne Slater | Brianne Slater |
| Scr | Mr Tack | | Dawn P. Williams | Scanden Stables |
Time: 1.58 2/5
Third Race: The John D. Bowling Memorial Maiden Hurdle
| Place | Horse | Rider | Trainer | Owner |
| 1 | Unbeliever | Darren Nagle | Desmond Fogarty | Irvin S. Naylor |
| 2 | Fiesty Lady | Jacob Roberts | Michael Leaf | Michael Leaf |
| 3 | Uncle Nutty | James Slater | Brianne Slater | Brianne Slater |
| 4 | Evarts | Paddy Young | Leslie F. Young | Silverton Hill LLC |
| Scr | Lonesome Nun | | F. Bruce Miller | Blythe Miller Davies |
Time: 3:30 1/5
Fourth Race: The Benjamin H. C. Bowie Memorial Novice Timber
| Place | Horse | Rider | Trainer | Owner |
| 1 | Volle Nolle |
Paddy Young |
Regina Welsh | Northwoods Stable |
| 2 | Gypsy Beads | Diana Gillam | Jeremy Gillam | Jeremy Gillam |
| 3 | Excentrikbydesign | Darren Nagle | Desmond Fogarty | Irvin S. Naylor |
| 4 | Mr. Pike | Jody Petty | Todd J. Wyatt | Cary W. Jackson |
| DQ | Fond Of A Drop (GB) | Gus Brown | Richard L. Valentine | Anna Stable |
| F | Monarch Lane | James Slater | Charles C. Fenwick, Jr. | H. Bruce Fenwick |
| Scr | Mr Tack | Patrick Worrall | Dawn P. Williams | Scanden Stables |
Time: 6:36 2/5
Fifth Race: The Annapolis Subscription Plate Amateur Flat.
| Place | Horse | Rider | Trainer | Owner |
| 1 | Bag Of Hammers | Gus Brown | Brianne Slater | Irvin S. Naylor |
| 2 | Lonesome Nun | Keri Brion | F. Bruce Miller | Blythe Miller Davies |
| 3 | Best Attack | Becky Dang | F. Bruce Miller | Octoraro Stables LLC |
| 4 | General Roanoke | Paul Madden | Joseph C. Walsh | Cranmore Stables |
| 5 | Foyle | Patrick Worrall | Dawn P. Williams | H. Bruce Fenwick |
| 6 | Patriot's Path | Desmond Fogarty | Desmond Fogarty | Irvin S. Naylor |
| 7 | Bold Quest | Connor Hankin | Regina Welsh | Northwoods Stable |
| 8 | Colonial Kid | Robert Bennett | Brianne Slater | Irvin S. Naylor |
| 9 | Sword Of Dubai | | Katherine N. McKenna | Katherine N. McKenna |
| 10 | Best Alibi (Ire) | Darren Nagle | Desmond Fogarty | Irvin S. Naylor |
| Scr | Wolfe Tone | Darren Nagle | Desmond Fogarty | Irvin S. Naylor |
| Scr | Spinning Sound (Ire) | Jake Chalfin | Ricky Hendriks | Debra E. Kachel |
| Scr | St Of Circumstance | Todd McKenna | Todd McKenna | Keystone Thoroughbreds |
| Scr | Dynaskill | | F. Bruce Miller | Octoraro Stables LLC |
| Scr | Year Of The City | Suzanne Stettinius | Suzanne Stettinius | Mint Meadows Farm |
| Scr | You The Man | Blair Wyatt | Todd J. Wyatt | William D. Fossett |
Time: 3:48 4/5
Sixth Race: The Raborg Maiden Maiden Hurdle
| Place | Horse | Rider | Trainer | Owner |
| 1 | Bermuda | Paddy Young | Leslie F. Young | Diamond M Racing and John Hawks |
| 2 | Rippin And Runnin | Darren Nagle | Richard L. Valentine | Magalen O. Bryant |
| DQ | Furtive | Diana Gillam | Jeremy Gillam | Jeremy Gillam |
| F | Quiet Approval | Jacob Roberts | Katherine N. McKenna | Move Up Stable |
Seventh Race: $5,000. The John Murray Begg Memorial Open Timber
| Place | Horse | Rider | Trainer | Owner |
| 1 | Radio Flyer (Ire) | Gus Brown | Richard L. Valentine | Augustin Stables |
| 2 | Take Harry | Jacob Roberts | Alicia S. Murphy | Sportsmans Hall |
| 3 | Bequeathed | Patrick Worrall | Dawn P. Williams | Scanden Stables |
Time: 6:23 1/5
Eighth Race: The Trident Plate Open Flat
| Place | Horse | Rider | Trainer | Owner |
| 1 | Brother Sy | Travis Kinnamon | Wendy Kinnamon | Tee Time Stable |
| 2 | Dubai Sunday (Jpn) | Darren Nagle | Desmond Fogarty | Irvin S. Naylor |
| 3 | Grinding Speed | Jacob Roberts | Alicia S. Murphy | Michael T. Wharton |
| 4 | Secret Style | Paddy Young | Ricky Hendriks | Debra E. Kachel |
| 5 | Snubbed | Diana Gillam | Jeremy Gillam | Jeremy Gillam |
| 7 | Dynaskill | | F. Bruce Miller | Octoraro Stables LLC |
| LR | Love Tour | Cameron Frock | Charles Frock | C & B Stable |
| Scr | Better With Butter | Sherry Hanscom | Justin Nixon | Fred Nixon |
| Scr | Dan's Edith | Jason Clayton | Bill Sienkewicz | Bill Sienkewicz |
| Scr | Kincarey | Anthony Aguirre | Cosette Busquets | Garboso, Inc. |
| Scr | One Golden Minute | Anthony Aguirre | Cosette Busquets | Garboso, Inc. | >
Time: 1:51 1/5
Ninth Race: The Mattaponi Open Flat.
| Place | Horse | Rider | Trainer | Owner |
| 1 | C R's Deputy | Paddy Young | Ricky Hendriks | Barracuda Racing Stable |
| 2 | Jellyberry |
Becky Dang |
F. Bruce Miller | Octoraro Stables LLC |
| 3 | Waltzing Bear | Diana Gillam | Jeremy Gillam | Jeremy Gillam |
| 4 | Kincarey | Anthony Aguirre | Cosette Busquets | Garboso, Inc. |
| Scr | Azulyekit | Paul Madden | Joseph C. Walsh | J. Walsh & C. McCullagh |
| Scr | One Golden Minute | Anthony Aguirre | Cosette Busquets | Garboso, Inc. |
| Scr | Classical Master | | Brad MacKinnon | Ragtime Stable |
| Scr | Free Again | Cameron Frock | Charles Frock | C & B Stable |
| Scr | Cover My Six | Sherry Hanscom | Justin Nixon | Fred Nixon |
| Scr | Spinning Sound (Ire) | Jake Chalfin | Ricky Hendriks | Debra E. Kachel |
Marlborough reported that the jockeys had followed instruction in the overnight which was 1 mile, but stewards followed the program which was 2 miles. Video was used to determine winner after 1 mile.
Tenth Race: The Lansdale G. Sasscer Memorial Junior Flat
| Place | Horse | Rider | Trainer | Owner |
| 1 | Dixie Colony | Erin Nolan | Ricky Hendriks | Debra E. Kachel |
| 2 | Ice Is Nice | Tate Shaw | Tate Shaw | Tate Shaw |
| 3 | Danesfort | Macaulay Kinnamon | Macaulay Kinnamon | Macaulay Kinnamon |
| 4 | Call Me Sonny | Scott Wolfendale | J. B. Secor | J. B. Secor |
| Scr | Year Of The City | Quinn Scala | Suzanne Stettinius | Mint Meadows Farm |
| Scr | Bold Quest | Connor Hankin | Regina Welsh | Northwoods Stable |
Time: 1:57
Eleventh Race: Governor's Cup Hunt Club Challenge Hunt Team Relay
| Place | Team |
| 1 |
HCIB Hounds |
| 2 | Marlborough Hunt |
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