First Race Small Ponies
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Cpl. Kirk J. Bosselmann Memorial Races Small Pony. About 1/2 mile on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Jasper | | | Christopher Talley | Kelsey Lefever | Kelsey Lefever | |
| 2 | Missy | | | Kellie Witte | Kellie Witte | Kellie Witte | |
| 3 | Blueberry Muffin | | | Erin Swope | Erin Swope | Erin Swope | |
| 4 | Emmy-Lou | | | Alexandra Vest | Mint Meadows Farm | Suzanne Stettinius | |
| 5 | Cricket | | | Darby Hyde | Darby Hyde | Darby Hyde | |
Winning Margin: 3   Winning Time: :36 3/5   Turf: yielding
Jasper, wh. g. 2004
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Medium Ponies
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Cpl. Kirk J. Bosselmann Memorial Races Medium Pony. About 1/2 mile on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Jasper | | | Christopher Talley | Kelsey Lefever | Kelsey Lefever | |
| OC | Annabelle | | | Trevor McCarthy | Suzy Armacost | Michael J. McCarthy | |
| OC | Domino Effect | | | Catie Keil | Catie Keil | Catie Keil | |
Winning Margin: 6   Winning Time: :50 3/5   Turf: yielding
Jasper, wh. g. 1999
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Large Ponies
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Cpl. Kirk J. Bosselmann Memorial Races Large Pony. About 1/2 mile on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Pepper | | | Emma M. Warden | Emma M. Warden | Emma M. Warden | |
| 2 | Glenmore Secret Romance | | | Eric Poretz | Eric Poretz | Eric Poretz | |
| 3 | Show A Little Acre | | | Scarlett Lovett | Scarlett Lovett | Scarlett Lovett | |
| 4 | Ace Of Spades | | | Scott Wolfendale | Scott Wolfendale | Scott Wolfendale | |
| 5 | Sunny | | | Michael Ried | Clifton Budd | Clifton Budd | |
| 6 | Watch Me Wiggle | | | Christopher Talley | Kelsey Lefever | Kelsey Lefever | |
Winning Margin: 7   Winning Time: :44 1/5   Turf: yielding
Pepper, b. m. 1990, by Habanero - Cayenne, by .
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Second Race
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Restricted Young Adult Flat. About 1 mile on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Sailmaker | | | Sarah Green | Mint Meadows Farm | Suzanne Stettinius | |
| 2 | Untamed Hero | | | Scarlett Lovett | Scarlett Lovett | Scarlett Lovett | |
| 3 | Carlet | | | Gina Perri | F. Bruce Miller | F. Bruce Miller | |
| 4 | Ambassador Dan | | | Meredith Almony | James Tepedino | Suzy Armacost | |
| 5 | Smooth Flight | | | Emma M. Warden | Suzanne Stettinius | Suzanne Stettinius | |
| 6 | Smokey | | | Tate Shaw | Thistledown Farm | Tate Shaw | |
| 7 | Rare Attitude | | | Lacey Velleggia | Suzy Armacost | Suzy Armacost | |
Winning Margin:   Winning Time: 1:37 3/5   Turf: yielding
Sailmaker, dk.b./br. m. 2000, by Partner's Hero - Smartest, by Smarten. Bred by Sheila Williams (Md)
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Third Race
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$1,000. Maiden Hurdle Emergent Biosolutions
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | What a Warrior | | 155 | Carl Rafter | Thomas A. Hulfish, III | Mrs. D. M. Smithwick | |
| 2 | Ouagadougou | | 155 | Jeff Murphy | Northfield Farm, LLC | Edward Mulligan | |
| 3 | Devil's Preacher | | 155 | Colvin Ryan | Colvin G. Ryan | Julie Gomena | |
| PU | Prettymarsh | | 147 | Xavier Aizpuru | Mrs. Rufus M.G. Williams | Jack Fisher | |
| PU | Unbeliever | | 155 | Darren Nagle | Irvin S. Naylor | Desmond Fogarty | |
Winning Margin: 1   Winning Time: 4:46 1/5   Turf: yielding
What a Warrior, dk.b./br. g. 2003, by Crowd Pleaser - What A Gaylord, by Lord Gaylord. Bred by John A. Guest & Barbara A. Anderson (Md)
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Fourth Race
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$7,500. Preakness Open Timber
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Won Wild Bird | | 157 | Carl Rafter | Anne O. Haynes | Regina Welsh | |
| 2 | Endless Mountain | | 165 | Jeff Murphy | Indian Run Farm | Mrs. D. M. Smithwick | |
| 3 | Shady Valley | | 165 | Russell Haynes | Anne O. Haynes | Regina Welsh | |
| 4 | Brogans Shield | | 165 | Michael Cooney | Beth deStanley | Beth deStanley | |
| 5 | Wazee Moto | | 165 | Melanie Williams | Vicki Bower | Jazz Napravnik | |
| 6 | Can't Find My Keys | | 165 | Mark Watts | Louis Neilson, III | Louis Neilson, III | |
| 7 | Bequeathed | | 165 | Patrick Worrall | Scanden Stable | Dawn P. Williams | |
| 8 | Incaseyouraminer | | 165 | Benjamin Swope | Benjamin C. Swope | Benjamin C. Swope | |
| PU | Volle Nolle | | 165 | James Slater | Northwoods Stable | Regina Welsh | |
| PU | Bisque d'jour | | 165 | Darren Nagle | Barbara Smith & Carole Garcia | Barbara Smith | |
Winning Margin: 1/2   Winning Time: 6:51 1/5   Turf: yielding
Won Wild Bird, gr./ro. m. 2002, by Wild Wonder - Rowdy Bird, by Topsider. Bred by Anne O. Haynes (Fl)
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Fifth Race
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Preakness Ladies Open Flat Lady Rider Flat. About 1 1/2 miles on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Green Velvet | | 142 | Suzanne Stettinius | Jennifer Pitts | Jazz Napravnik | |
| 2 | Class Century | | 145 | Melanie Williams | Mede Cahaba Stable & Stud LLC | Lilith Boucher | |
| 3 | Lonesome Nun | | 142 | Becky Dang | Blythe Miller Davies | F. Bruce Miller | |
| 4 | Miss Diggy Bear | | 137 | Paige McPherson | Jason L. Cole | Jason L. Cole | |
| LR | Joshua G. | | 145 | Filippa Boughton | Jason L. Cole | Jason L. Cole | |
Winning Margin: 1/2   Winning Time: 2:31 1/5   Turf: yielding
Green Velvet, b. f. 2005, by Petitionville - Green Jeans, by Green Dancer. Bred by Althea D. Richards (Va)
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Sixth Race
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$7,500. Preakness Open Hurdle
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | One Sea | | 155 | Roddy Mackenzie | Randolph D. Rouse | Randolph D. Rouse | |
| 2 | Church Ghost | | 155 | Jeff Murphy | Jake Dunning | Edward Mulligan | |
| 3 | Swimming River | | 155 | Mark Watts | Joseph K. Kornfeind | Paul A. Rowland | |
| 4 | Scandalizer | | 147 | Jacob Roberts | Peter Hitchen | Mrs. D. M. Smithwick | |
| DQ | Best Name (GB) | | 155 | Darren Nagle | Irvin S. Naylor | Desmond Fogarty | |
| F | Class Real Rock | | 150 | Richard Boucher | Mede Cahaba Stable & Stud LLC | Lilith Boucher | |
| LR | Easy Escapade | | 155 | Sam Cockburn | David Benson | David Benson | |
| PU | Just A Prince (NZ) | | 155 | Jake Chalfin | Indian Run Farm | Mrs. D. M. Smithwick | |
| PU | Otappaz | | 155 | James Slater | Charles J. McCann | Charles J. McCann | |
Winning Margin: 1 1/2   Winning Time: 4:43 1/5   Turf: yielding
One Sea, b. g. 2000, by Sea Hero - Early Maud, by Groovy. Bred by Estate of Walter M. Jeffords, Jr. (Ky)
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Seventh Race
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$2,500. Preakness Novice Timber
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Cool Fellow | | 170 | Carl Rafter | Beth deStanley & Allen K. Shreve | Beth deStanley | |
| 2 | Bon Caddo | | 175 | Patrick Worrall | H. Bruce Fenwick | Dawn P. Williams | |
| 3 | Dreaming Of Glory | | 157 | Kim Vest | Kim Wirtanen Vest | Kim Wirtanen Vest | |
| 4 | Excentrikbydesign | | 165 | Darren Nagle | Irvin S. Naylor | Desmond Fogarty | |
| 5 | Instamatic | | 165 | Steve Green | Wheatland Farm | Steve Green | |
| LR | Template | | 165 | Jacob Roberts | Move Up Stable | Alicia S. Murphy | |
| PU | First Effort | | 165 | Sam Cockburn | Rehilian Racing Stable | David M. Bourke | |
| PU | Inca Magic | | 165 | James Slater | Landslide Farm | Cyril Murphy | |
| PU | Crimson Lode | | 165 | Michael Cooney | DMC Stable | Diana L. McClure | |
| PU | Bold Quest | | 170 | Jeff Murphy | Northwoods Stable | Regina Welsh | |
Winning Margin: 8   Winning Time: 5:52 3/5   Turf: yielding
Cool Fellow, gr. g. 2000, by The Cool Virginian - Lucky Issy, by Northern Raja. Bred by W. Gary Baker (Md)
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Eighth Race
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$1,000. Washington DC International Open Flat. About 1 3/4 miles on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Organizer | | 155 | Nial Molloy | Majesty Stud, LLC | Paul A. Rowland | |
| 2 | Berchta's Brew | | 155 | Nick Carter | W. L. & D. J. Aylor, Jr. | William Aylor, Jr. | |
| 3 | Lenny | | 155 | Michael Cooney | Hilltop Farm | Diana L. McClure | |
| 4 | Siren's Echo | | 147 | Darren Nagle | Irvin S. Naylor | Desmond Fogarty | |
| 5 | Sudden Concern | | 155 | Bruce Daley | W. Gary Baker | Mrs. D. M. Smithwick | |
| 6 | Bad Birdie | | 155 | Barry Duncan | Nicholas Yazdani | Fred H. Duncan | |
| 7 | Rahy Bird | | 147 | Jorge Torres | Lilith Boucher | Lilith Boucher | |
| 8 | Ha Sohn | | 155 | Benjamin Swope | Benjamin C. Swope | Benjamin C. Swope | |
| 9 | Tough Jake | | 155 | Adam Newman | Adam Newman | Janet E. Elliot | |
| DQ | Hot For You | | 155 | Steve Currey | Steve Currey | Steve Currey | |
| DQ | Royal Quoit | | 155 | James Slater | Landslide Farm | Cyril Murphy | |
| PU | Maximize | | 155 | Sam Cockburn | Gordon C. Keys | Bay C. Cockburn | |
| PU | Goldie | | 147 | Roddy Mackenzie | Randolph D. Rouse | Randolph D. Rouse | |
Winning Margin: 10   Winning Time: 3:39   Turf: yielding
Organizer, dk.b./br. h. 2002, by Raffie's Majesty - Treasure Always, by Summer Squall. Bred by Majesty Stud, LLC (NY)
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