| All-Comers Meet at Southern September 5, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Severna Park | 15 | 12th | Matt Fontaine | 20:50 | |
| 2 | Chesapeake | 76 | 15th | Sam Phipps | 21:24 | |
| 3 | Arundel | 105 | 16th | Andrew Brennan | 21:29 | |
| 4 | South River | 108 | 32nd | Tyler Stocksdale | 22:36 | |
| 5 | Northeast | 108 | 45th | Patrick Michalski | 23:18 | |
| 6 | Southern | 116 | 46th | Kerry Toole | 23:24 | |
| 57th | Chris Casey | 23:48 | ||||
| 59th | Michael Ferguson | 23:57 | ||||
| 60th | Mitch Kammer | 24:03 | ||||
| 63rd | Brandon Gruszczynski | 24:27 | ||||
| 64th | Mark Ritterpusch | 24:29 | ||||
| 65th | Mike Stewart | 24:30 | ||||
| 69th | Robby Tollett | 25:00 | ||||
| 70th | Daniel Hendrix | 25:01 | ||||
| 83rd | Mike Goldstraw | 26:33 | ||||
| 84th | Patrick May | 27:11 | ||||
| 88th | Scott Krozack | 27:59 | ||||
| 89th | Alec Keeter | 28:14 | ||||
| 97th | Alex Gibson | 31:56 | ||||
| 99th | Steven Meyer | 33:02 | ||||
| South River September 10, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Severna Park | 29 | 2nd | William Neal | 17.16 | |
| 2 | Chesapeake | 43 | 7th | TJ Myers | 18.06 | |
| 3 | Meade | 95 | 8th | Ripken LaMarsh | 18.10 | |
| 4 | Northeast | 104 | 12th | Phil Trainor | 19.06 | |
| 5 | North County | 123 | 14th | Chris Seto | 19.10 | |
| 6 | Annapolis | 153 | 16th | Collin Wojciechowski | 19.21 | |
| 17th | Dan Fontaine | 19.24 | ||||
| 21st | Tim Wickless | 19.35 | ||||
| 24th | DJ Drexel | 19.47 | ||||
| 29th | Sam Phipps | 20.07 | ||||
| 31st | Patrick Smith | 20.28 | ||||
| 33rd | Matt Fontaine | 20.36 | ||||
| 41st | Tyler Stocksdale | 21.11 | ||||
| 44th | Adam Blevins | 21.21 | ||||
| 45th | Mike Smith | 21.23 | ||||
| 46th | Andrew Brennan | 21.24 | ||||
| 58th | Kerry Toole | 22.14 | ||||
| 61st | Patrick Michalski | 22.23 | ||||
| 65th | Mark Ritterpusch | 22.31 | ||||
| 68th | Mike Stewart | 22.38 | ||||
| 71st | Jarred Reusing | 22.46 | ||||
| 73rd | Chris Casey | 22.55 | ||||
| 75th | Michael Ferguson | 22.59 | ||||
| 78th | Mitch Kammer | 23.12 | ||||
| 84th | Brandon Gruszczynski | 23.33 | ||||
| 86th | Mike Goldstraw | 24.12 | ||||
| 88th | Daniel Hendrix | 24.14 | ||||
| 90th | Robby Tollet | 24.38 | ||||
| 98th | Scott Krozack | 25.43 | ||||
| 99th | Patrick May | 25.50 | ||||
| 104th | Alex Gibson | 28.13 | ||||
| 105th | Andrew Meyer | 30.26 | ||||
| 106th | Steven Meyer | 31.28 | ||||
| Knights Invitational September 19, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Archbishop Spalding | 94 | 9th | Will Neal | 16:04 | |
| 2 | Severna Park | 95 | 17th | Ripken LaMarsh | 16:33 | |
| 3 | Leonardtown | 123 | 23rd | TJ Myers | 16:43 | |
| 4 | DeMatha Catholic | 136 | 50th | Chris Seto | 17:36 | |
| 5 | Chesapeake | 162 | 63rd | Phil Trainor | 17:59 | |
| 6 | Northern | 167 | 73rd | Collin Wojciechowski | 18:19 | |
| 7 | Broadneck | 189 | 87th | Dan Fontaine | 18:38 | |
| 8 | Annapolis | 193 | ||||
| 9 | Meade | 219 | ||||
| 10 | Oakland Mills | 260 | ||||
| 11 | South River | 295 | ||||
| 12 | Arundel | 328 | ||||
| 13 | Old Mill | 359 | ||||
| 14 | John Carroll | 402 | ||||
| 15 | Northeast | 408 | ||||
| 16 | Aberdeen | 419 | ||||
| 17 | Paint Brach | 442 | ||||
| 18 | Queen Anne's | 472 | ||||
| 19 | Thomas Stone | 580 | ||||
| 20 | Saint Mary's | 596 | ||||
| "B" Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| Tim Wickless | 17.51 | |||||
| Sam Phipps | 18.04 | |||||
| DJ Drexel | 18.28 | |||||
| Patrick Smith | 19.03 | |||||
| Mike Smith | 19.14 | |||||
| Tyler Stocksdale | 19.23 | |||||
| Matt Fontaine | 19.26 | |||||
| Jarred Reusing | 19.48 | |||||
| Andrew Brennan | 19.49 | |||||
| Mark Ritterpusch | 20.05 | |||||
| Adam Blevins | 20.17 | |||||
| Michael Ferguson | 20.19 | |||||
| Kerry Toole | 20.37 | |||||
| Patrick Michalski | 20.43 | |||||
| Robby Tollett | 21.03 | |||||
| Chris Casey | 21.04 | |||||
| Mike Stewart | 21.11 | |||||
| Mitch Kammer | 21.13 | |||||
| Daniel Hendrix | 21.39 | |||||
| Brandon Gruszczynski | 21.54 | |||||
| Mike Goldstraw | 22.34 | |||||
| Christopher Taylor | 22.44 | |||||
| Scott Krozack | 23.26 | |||||
| Patrick May | 23.45 | |||||
| AJ Keeter | 23.58 | |||||
| Joseph Degreenia | 24.27 | |||||
| Alex Gibson | 25.30 | |||||
| Andrew Meyer | 25.36 | |||||
| Steven Meyer | 27.52 | |||||
| Frank Keyser Invitational October 4, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | South Lakes | 48 | 1st | William Neal | 15:52 | |
| 2 | Thomas Johnson | 78 | 3rd | Ripken LaMarsh | 16:28 | |
| 3 | Chesapeake | 86 | 24th | Tim Wickless | 17:21 | |
| 4 | Linganore | 91 | 28th | Sam Phipps | 17:33 | |
| 5 | Urbana | 122 | 30th | Phil Trainor | 17:46 | |
| 6 | Musselman | 161 | 37th | Dan Fontaine | 17:52 | |
| 7 | Clarksburg | 202 | 38th | DJ Drexel | 17:58 | |
| 8 | Frederick | 227 | ||||
| 9 | Blake | 254 | ||||
| 10 | Martinsburg | 270 | ||||
| 11 | Tuscarora | 301 | ||||
| 12 | Great Mills | 322 | ||||
| 13 | Seneca Valley | 340 | ||||
| "B" Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1st | Kyle Fairchild | 17:19 | ||||
| 17th | Collin Wojciechowski | 18:16 | ||||
| 40th | Mike Smith | 19:00 | ||||
| 49th | Tyler Stocksdale | 19:14 | ||||
| 52nd | Matt Fontaine | 19:18 | ||||
| 53rd | Andrew Brennan | 19:18 | ||||
| 62nd | Brandon Gruszczynski | 19:33 | ||||
| 68th | Michael Ferguson | 19:44 | ||||
| 76th | Adam Blevins | 19:49 | ||||
| 86th | Chris Casey | 20:13 | ||||
| 90th | Mark Ritterpusch | 20:21 | ||||
| 92nd | Mike Stewart | 20:28 | ||||
| 96th | Mike Goldstraw | 20:31 | ||||
| 98th | Jarred Reusing | 20:34 | ||||
| 103rd | Patrick Michalski | 20:41 | ||||
| 117th | Robby Tollett | 21:03 | ||||
| 118th | Mitch Kammer | 21:05 | ||||
| 130th | Daniel Hendrix | 21:22 | ||||
| 157th | Scott Krozack | 22:25 | ||||
| 158th | AJ Keeter | 22:26 | ||||
| 161st | Chris Taylor | 22:33 | ||||
| 163rd | Joseph Degreenia | 22:39 | ||||
| 184th | Patrick May | 23:52 | ||||
| 191st | Alex Gibson | 24:49 | ||||
| 205th | Steven Meyer | 27:24 | ||||
| Meade Autumn Classic October 11, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Richard Montgomery | 35 | 5th | Kyle Fairchild | 17:56 | |
| 2 | Meade | 36 | 24th | Andrew Brennan | 19:58 | |
| 3 | Old Mill | 114 | 25th | Adam Blevins | 19:58 | |
| 4 | Severna Park | 121 | 40th | Brandon Gruszczynski | 20:27 | |
| 5 | Chesapeake | 137 | 49th | Michael Ferguson | 21:01 | |
| 6 | Southern | 175 | 52nd | Mark Ritterpusch | 21:12 | |
| 7 | Patuxent | 177 | 73rd | Chris Casey | 23:30 | |
| 8 | South River | 192 | ||||
| 9 | Kennedy | 203 | ||||
| 10 | Broadneck | 239 | ||||
| 11 | Glenelg | 329 | ||||
| 12 | Northeast | 340 | ||||
| "B" Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Richard Montgomery | 19 | B21st Kerry Toole | 21:31 | ||
| 2 | Severna Park | 65 | B24th Mike Stewart | 21:46 | ||
| 3 | Old Mill | 110 | B29th Mitch Kammer | 22:06 | ||
| 4 | Chesapeake | 121 | B32nd Jarred Reusing | 22:10 | ||
| 5 | Wheaton | 124 | B34th Patrick Michalski | 22:18 | ||
| 6 | Broadneck | 136 | B47th Robby Tollett | 23:12 | ||
| 7 | Patuxent | 185 | B50th Mike Goldstraw | 23:23 | ||
| 8 | Southern | 187 | C11th Daniel Hendrix | 21:59 | ||
| C28th AJ Keeter | 24:12 | |||||
| C29th Scott Krozack | 24:18 | |||||
| C34th Patrick May | 24:59 | |||||
| C37th Alex Gibson | 26:44 | |||||
| C44th Steven Meyer | 29:03 | |||||
| Hereford October 11, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Mount Hebron | 48 | 7th | Will Neal | 17:17 | |
| 2 | Bel Air | 59 | 19th | TJ Myers | 18:02 | |
| 3 | Jefferson (WV) | 86 | 20th | Ripken Lamarsh | 18:08 | |
| 4 | Chesapeake | 101 | 35th | Tim Wickless | 18:49 | |
| 5 | Century | 119 | 44th | Phil Trainor | 19:03 | |
| 6 | Loch Raven | 127 | 46th | Sam Phipps | 19:05 | |
| 7 | South River | 197 | 47th | Chris Seto | 19:10 | |
| 8 | Aberdeen | 230 | Collin Wojciechowski | 19:17 | ||
| Dan Fontaine | 19:37 | |||||
| DJ Drexel | 19:38 | |||||
| Patrick Smith | 20:40 | |||||
| Mike Smith | 20:47 | |||||
| Matt Fontaine | 21:12 | |||||
| Tyler Stocksdale | 21:23 | |||||
| Chesapeake October 15, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Chesapeake | 22 | 1st | Will Neal | 16:33 | |
| 2 | Arundel | 87 | 3rd | Kyle Fairchild | 16:48 | |
| 3 | Meade | 99 | 5th | Ripken LaMarsh | 16:56 | |
| 4 | Northeast | 102 | 6th | Tim Wickless | 17:16 | |
| 5 | Old Mill | 118 | 7th | TJ Myers | 17:35 | |
| 6 | Glen Burnie | 151 | 8th | Chris Seto | 17:47 | |
| 7 | North County | 159 | 13th | collin Wojciechowski | 18:00 | |
| 14th | Phil Trainor | 18:07 | ||||
| 17th | Sam Phipps | 18:13 | ||||
| 19th | Dan Fontaine | 18:32 | ||||
| 20th | DJ Drexel | 18:38 | ||||
| 27th | Andrew Brennan | 19:10 | ||||
| 28th | Patrick Smith | 19:14 | ||||
| 38th | Matt Fontaine | 19:43 | ||||
| 41st | Mike Smith | 20:00 | ||||
| 47th | Tyler Stocksdale | 20:21 | ||||
| 50th | Michael Ferguson | 20:23 | ||||
| 52nd | Adam Blevins | 20:31 | ||||
| 53rd | Brandon Gruszczynski | 20:34 | ||||
| 54th | Kerry Toole | 20:37 | ||||
| 55th | Mark Ritterpusch | 20:48 | ||||
| 58th | Patrick Michalski | 21:06 | ||||
| 60th | Jarred Reusing | 21:09 | ||||
| 62nd | Mike Stewart | 21:21 | ||||
| 63rd | Daniel Hendrix | 21:31 | ||||
| 65th | Tyler Trainor | 21:46 | ||||
| 72nd | Mitch Kammer | 22:44 | ||||
| 74th | Mike Goldstraw | 22:45 | ||||
| 78th | Chris Taylor | 22:49 | ||||
| 81st | Robby Tollett | 22:54 | ||||
| 84th | AJ Keeter | 23:32 | ||||
| 85th | Joseph Degreenia | 23:39 | ||||
| 88th | Patrick May | 23:50 | ||||
| 91st | Scott Krozack | 24:54 | ||||
| 92nd | Alex Gibson | 25:03 | ||||
| 100th | Steven Meyer | 26:59 | ||||
| County Championships October 23, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Severna Park | 48 | 4th | Will Neal | 16:35 | |
| 2 | Chesapeake | 76 | 13th | Ripken LaMarsh | 17:17 | |
| 3 | Annapolis | 98 | 16th | TJ Myers | 17:26 | |
| 4 | Meade | 106 | 17th | Kyle Fairchild | 17:28 | |
| 5 | Broadneck | 107 | 26th | Tim Wickless | 17:48 | |
| 6 | Arundel | 169 | 32nd | Chris Seto | 18:07 | |
| 7 | South River | 170 | 40th | Collin Wojciechowski | 18:54 | |
| 8 | Old Mill | 186 | ||||
| 9 | Northeast | 201 | ||||
| 10 | Southern | 268 | ||||
| "B" Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Severna Park | 33 | 4th | Phil Trainor | 18:38 | |
| 2 | Chesapeake | 44 | 5th | Sam Phipps | 18:45 | |
| 3 | Broadneck | 49 | 6th | DJ Drexel | 18:46 | |
| 4 | North County | 132 | 8th | Dan Fontaine | 18:54 | |
| 5 | Arundel | 152 | 28th | Patrick Smith | 19:42 | |
| 6 | South River | 160 | 29th | Andrew Brennan | 19:42 | |
| 7 | Annapolis | 200 | 39th | Matt Fontaine | 20:02 | |
| 8 | Old Mill | 227 | 46th | Tyler Stocksdale | 20:11 | |
| 9 | Southern | 233 | 48th | Adam Blevins | 20:16 | |
| 50th | Mike Smith | 20:17 | ||||
| 66th | Mark Ritterpusch | 20:51 | ||||
| 68th | Brandon Gruszczynski | 20:52 | ||||
| 69th | Jarred Reusing | 20:53 | ||||
| 71st | Michael Ferguson | 20:59 | ||||
| 72nd | Tyler Trainer | 21:02 | ||||
| 74th | Kerry Toole | 21:08 | ||||
| 81st | Patrick Michalski | 21:27 | ||||
| 82nd | Mike Stewart | 21:28 | ||||
| 101st | Mitch Kammer | 21:56 | ||||
| 117th | Mike Goldstraw | 22:40 | ||||
| 127th | Daniel Hendrix | 22:56 | ||||
| 128th | Chris Taylor | 22:59 | ||||
| 130th | Chris Casey | 23:03 | ||||
| 139th | AJ Keeter | 23:20 | ||||
| 140th | Scott Krozack | 23:21 | ||||
| 143rd | Joseph Degreehia | 23:42 | ||||
| 144th | Robby Tallett | 23:45 | ||||
| 146th | Patrick May | 24:06 | ||||
| 156th | Alex Gibson | 26:10 | ||||
| 164th | Steven Meyer | 29:32 | ||||
| Region Championships October 30, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Severna Park | 41 | 2nd | Will Neal | 15:47 | |
| 2 | Leonardtown | 60 | 10th | Kyle Fairchild | 16:22 | |
| 3 | Chesapeake | 66 | 12th | Ripken LaMarsh | 16:27 | |
| 4 | Broadneck | 102 | 17th | TJ Myers | 16:33 | |
| 5 | South River | 131 | 25th | Tim Wickless | 17:03 | |
| 6 | Old Mill | 171 | 28th | Chris Seto | 17:22 | |
| 7 | Arundel | 172 | 31st | Phil Trainor | 17:41 | |
| 8 | Thomas Stone | 247 | ||||
| 9 | North County | 252 | ||||
| State Championships at Hereford November 8, 2008 |
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| Race Results | Chesapeake Team Standings | |||||
| Place | School | Points | Place | Name | Time | |
| 1 | Walter Johnson | 48 | 8th | Will Neal | 17:07 | |
| 2 | Severna Park | 139 | 30th | Ripken LaMarsh | 17:49 | |
| 3 | Northwest | 142 | 48th | Kyle Fairchild | 18:09 | |
| 4 | Sherwood | 169 | 75th | Tim Wickless | 18:34 | |
| 5 | Winston Churchill | 178 | 90th | TJ Myers | 18:47 | |
| 6 | Leonardtown | 197 | 97th | Phil Trainor | 18:58 | |
| 7 | Thomas Johnson | 215 | 99th | Chris Seto | 19:02 | |
| 8 | Chesapeake | 230 | ||||
| 9 | Gaithersburg | 260 | ||||
| 10 | Walt Whitman | 261 | ||||
| 11 | Magruder | 296 | ||||
| 13 | C. Milton Wright | 323 | ||||
| 14 | Eleanor Roosevelt | 347 | ||||
| 15 | North Carroll | 367 | ||||
| 16 | Broadneck | 368 | ||||
| 17 | Westminster | 399 | ||||
| 18 | Linganore | 404 | ||||
| 19 | South River | 452 | ||||
| 20 | Ch Flowers | 648 | ||||
| 21 | Wise | 649 | ||||