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First Race
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The Journey's End Bowl Novice Rider Flat. About 1 1/2 miles on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Chivite (Ire) | | 160 | Becky Dang | Mrs. Calvin Houghland | F. Bruce Miller | |
| 2 | Class Deputy | | 160 | Hayleigh Royston | Jacob Deane | Mark Deane | |
| 3 | Justabud | | 160 | Ben Garner | W. Gary Baker | Mrs. D. M. Smithwick | |
| 4 | In No Time | | 160 | Muiris Hinchion | Donald Yovanovich | Donald Yovanovich | |
| 5 | That Dream Cat | | 152 | Vika Monroe | Vika Monroe | William Aylor, Jr. | |
Chivite ran with most of the field just off That Dream Cat's early pace. When That Dream Cat fell back Class Deputy took the lead with Chivite close behind. Chivite made the lead at the head of the stretch and outfinished Class Deputy.
Winning Margin: 1 Winning Time: 2:28 3/5 Turf: firm
Chivite (Ire), b. g. 1999, by Alhaarth - Laura Margaret, by Persian Bold (Ire). Bred by B. Kennedy (Ire)
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Second Race
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The Middleburg Hunt Cup Amateur/Novice Rider Hurdle. About 2 1/8 miles over National Fences
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Marino Feliz (Chi) | | 170 | William Santoro | W. Gary Baker | Mrs. D. M. Smithwick | |
| 2 | Church Ghost | | *170 | Jake Dunning | Jake Dunning | Edward Mulligan | |
| 3 | Harry's Crown | | *173 | Sam Cockburn | Aylor Racing Stable | William Aylor, Jr. | |
| 4 | Just A Prince (NZ) | | *170 | Ben Garner | Indian Run Farm | Mrs. D. M. Smithwick | |
| 5 | Easy Escapade | | *170 | Muiris Hinchion | David Benson | David Benson | |
Marino Feliz was rated off the early pace, joined the leaders, Church Ghost and Harry's Crown, approaching the last fence where they jumped as a team and won going away in the stretch.
Winning Margin: 6 Winning Time: 4:33 2/5 Turf: firm
Marino Feliz (Chi), ch. g. 1998, by Onward - Feliz (Chi), by Riverhill (Fr). Bred by Haras Dadinco (Chi)
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Third Race
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The Samuel E. Bogley Memorial Maiden Flat. About 1 1/4 miles on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Whodoyoucallit | | 150 | Sam Cockburn | Bay C. Cockburn | Bay C. Cockburn | |
| 2 | Swell Party | | 150 | Jeff Murphy | Betsy B. Mead | Doug Fout | |
| 3 | Cooper | | 160 | Jacob Roberts | Michael Leaf | Michael Leaf | |
| 4 | Its A School Night | | 150 | Matthew McCarron | Kinross Farm | Neil R. Morris | |
| 5 | Dynamic Rhythm | | 160 | Richard McWade | Lucy Horner | Barbara McWade | |
| 6 | Saracat | | 147 | Vika Monroe | Aylor Racing Stable | William Aylor, Jr. | |
| 7 | Western Select | | 150 | Mike Woodson | Larry Woodson | William Aylor, Jr. | |
| 8 | Fifty Grand | | 150 | Carl Rafter | William M. Backer | Charles J. McCann | |
| F | Ozz Zzzapper | | 142 | Alex Thomas | Warren Owens | William Aylor, Jr. | |
| Ref | Black Tie Night | | 160 | Muiris Hinchion | Randolph D. Rouse | Randolph D. Rouse | |
Whatdoyoucallit took the lead with a mile to run, opened a comfortable margin and held off Swell Party who rallied from far back.
Winning Margin: 3/4 Winning Time: 2:03 Turf: firm
Whodoyoucallit, ch. g. 2007, by Reparations - Ways Of Fate, by Roy. Bred by Bay C. Cockburn (WV)
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Fourth Race
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The Middleburg Bowl Maiden Timber. About 3 miles over Timber
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Template | | 165 | Jacob Roberts | Move Up Stable | Alicia S. Murphy | |
This race was a walkover.
Winning Margin: Winning Time: Turf: firm
Template, ch. g. 2002, by Desert Wine - Templin, by Temperence Hill. Bred by Jon W. Sather (WA)
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Fifth Race
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The Matthew Leslie Memorial Maiden Hurdle. About 2 1/8 miles over National Fences
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Daylight Fire | | 152 | Carl Rafter | Falcon Racing | Donald Yovanovich | |
| 2 | Magic Moonshine | | 155 | Matthew McCarron | Kristall Farm | Richard L. Valentine | |
| 3 | Sgt. Bart | | 160 | James Slater | William F. C. Marlow, Jr. | Jazz Napravnik | |
| 4 | Final Straw | | 155 | Liam McVicar | Ellen Clark | Edward Mulligan | |
| PU | Ardagh | | 147 | Jeff Murphy | Edward Mulligan | Edward Mulligan | |
Daylight Fire assumed command shortly after the start and was never threatened drawing away to win easily.
Winning Margin: 10 Winning Time: 4:30 4/5 Turf: firm
Daylight Fire, b. m. 2005, by Seeking Daylight - Fire The Deputy, by Deputy Minister. Bred by Edward P. Evans (Va)
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Sixth Race
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The Louis Leith Memorial Restricted Maiden Hurdle. About 2 1/8 miles over National Fences
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Rippin and Runnin | | 160 | Matthew McCarron | Magalen O. Bryant | Richard L. Valentine | |
| 2 | White Holiday | | 160 | Liam McVicar | Randleston Farm | Jimmy Day | |
| 3 | Personal Two | | 160 | Jeff Murphy | Magalen O. Bryant | Doug Fout | |
| 4 | Straightredcard | | 160 | Jacob Roberts | James M. Leckrone | Jazz Napravnik | |
| 5 | Amazin Sun | | 155 | Carl Rafter | Mrs. S. K. Johnston, Jr. | Jimmy Day | |
| PU | Glorious Bird | | 147 | James Slater | James M. Courtney | Jazz Napravnik | |
Rippin And Runnin was close up in the early going, took the lead down the backside the first time around and repulsed Personal Two's bid in the last quarter mile. White Holiday took second by a head over Personal Two but couldn't get to the winner in the stretch.
Winning Margin: 1 Winning Time: 4:37 2/5 Turf: firm
Rippin and Runnin, b. g. 2004, by Eastern Echo - Say Farewell, by Second Bar. Bred by Magalen O. Bryant (Md)
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Seventh Race
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The George Straub Memorial Open Flat. About 1 1/4 miles on the Turf
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| Order | Horse | | Wgt | Rider | Owner | Trainer | Purse |
| 1 | Legendary Pacer | | 160 | Carl Rafter | Vicki Fuller | Donald Yovanovich | |
| 2 | Victory Bound | | 170 | Simon Hobson | Simon Hobson | Simon Hobson | |
| 3 | Protocol Chief | | 160 | Bruce Daley | Randolph D. Rouse | Randolph D. Rouse | |
Legendary Pacer stalked Victory Bound until they raced down the backside where he took command and drew away to win very much in hand. This was trainer Don Yovanovich's second win of the day.
Winning Margin: 15 Winning Time: 2:00 1/5 Turf: firm
Legendary Pacer, ch. g. 2002, by Pentelicus - Karin Chriss, by Silver Hawk. Bred by Becky Winemiller (Fl)
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