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| WINCHESTER |
| 2008 SEASON (3-7) |
| Aug. 22 | Alexandria | W 41- 0 |
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| Aug. 29 | Northeastern | ot L 21-22 |
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| Sep. 5 | at Hagerstown | L 12-53 |
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| Sep. 12 | Union County | L 14-22 |
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| Sep. 19 | at Cambridge City Lincoln | W 28-20 |
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| Sep. 26 | at Union City | L 24-25 |
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| Oct. 3 | Jay County | L 26-32 |
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| Oct. 10 | at Tri | W 28-12 |
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| Oct. 17 | Centerville | L 0-49 |
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| Oct. 24 | at Elwood | L 20-44 |
sect |
| 2007 SEASON (5-5) |
| Aug. 17 | at Alexandria | W 41-20 |
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| Aug. 24 | at Northeastern | ot L 26-27 |
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| Aug. 31 | Hagerstown | L 13-33 |
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| Sep. 7 | at Union County | W 26- 6 |
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| Sep. 14 | Cambridge City Lincoln | W 35-16 |
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| Sep. 21 | Union City | W 50- 6 |
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| Sep. 28 | at Jay County | L 19-40 |
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| Oct. 5 | Tri | W 41-21 |
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| Oct. 12 | at Centerville | L 21-30 |
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| Oct. 19 | at Northwestern | L 0-26 |
sect |
| 2006 SEASON (5-5) |
| Aug. 18 | Elwood | L 13-33 |
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| Aug. 25 | Northeastern | W 21- 0 |
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| Sep. 1 | at Hagerstown | L 9-35 |
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| Sep. 8 | Union County | W 52- 0 |
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| Sep. 15 | at Cambridge City Lincoln | W 30-14 |
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| Sep. 22 | at Union City | W 20-12 |
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| Sep. 29 | Jay County | L 21-48 |
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| Oct. 6 | at Tri | otW 15-14 |
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| Oct. 13 | Centerville | L 13-14 |
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| Oct. 20 | at Alexandria | L 20-31 |
sect |
| 2005 SEASON (6-5) |
| Aug. 19 | at Elwood | L 6-38 |
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| Aug. 26 | at Northeastern | W 35- 7 |
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| Sep. 2 | Hagerstown | L 0- 7 |
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| Sep. 9 | at Union County | W 34- 0 |
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| Sep. 16 | Cambridge City Lincoln | W 34- 0 |
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| Sep. 23 | Union City | W 19- 6 |
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| Sep. 30 | at Jay County | L 14-50 |
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| Oct. 7 | Tri | W 41-14 |
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| Oct. 14 | at Centerville | L 21-28 |
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| Oct. 21 | at South Adams | W 21-14 |
sect |
| Oct. 28 | Oak Hill | L 8-10 |
sect |
| 2004 SEASON (10-1) |
| Aug. 20 | Elwood | W 39- 0 |
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| Aug. 27 | Northeastern | W 39- 0 |
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| Sep. 3 | at Hagerstown | W 54-14 |
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| Sep. 10 | Union County | W 41-13 |
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| Sep. 17 | at Cambridge City Lincoln | W 19-12 |
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| Sep. 24 | at Union City | W 34- 0 |
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| Oct. 1 | South Adams | W 27- 6 |
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| Oct. 8 | at Tri | W 18- 7 |
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| Oct. 15 | Centerville | W 21-14 |
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| Oct. 22 | Centerville | W 15- 6 |
sect |
| Oct. 29 | at Eastbrook | L 0-35 |
sect |
| 2003 SEASON (6-4) |
| Aug. 22 | at Elwood | W 39- 6 |
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| Aug. 29 | at Northeastern | W 12- 7 |
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| Sep. 5 | Hagerstown | W 33- 8 |
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| Sep. 12 | at Union County | W 48-19 |
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| Sep. 19 | Cambridge City Lincoln | L 3-19 |
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| Sep. 27 | Union City | L 0- 6 |
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| Oct. 3 | at South Adams | L 0-12 |
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| Oct. 10 | Tri | W 35- 0 |
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| Oct. 17 | at Centerville | W 25-22 |
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| Oct. 24 | at Eastbrook | L 7-71 |
sect |
| 2002 SEASON (10-2) |
| Aug. 23 | Elwood | W 6- 0 |
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| Aug. 30 | Northeastern | W 51- 0 |
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| Sep. 6 | at Hagerstown | W 48-14 |
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| Sep. 13 | Union County | W 61- 7 |
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| Sep. 20 | at Cambridge City Lincoln | W 56- 6 |
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| Sep. 27 | at Union City | W 48- 6 |
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| Oct. 4 | South Adams | W 21- 0 |
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| Oct. 11 | at Tri | L 14-20 |
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| Oct. 18 | Centerville | W 36- 0 |
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| Oct. 25 | Monrovia | W 28- 0 |
sect |
| Nov. 1 | at Triton Central | W 18-12 |
sect |
| Nov. 8 | Indianapolis Scecina | L 21-41 |
sect |
| 2001 SEASON (4-6) |
| Aug. 17 | at Elwood | L 13-32 |
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| Aug. 24 | at Northeastern | L 23-25 |
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| Aug. 31 | Hagerstown | L 20-41 |
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| Sep. 7 | at Union County | W 33-22 |
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| Sep. 14 | Cambridge City Lincoln | W 42- 0 |
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| Sep. 21 | Union City | W 16- 6 |
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| Sep. 28 | at South Adams | L 12-42 |
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| Oct. 5 | Tri | L 14-18 |
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| Oct. 12 | at Centerville | W 21-20 |
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| Oct. 19 | Speedway | L 6-16 |
sect |
| 2000 SEASON (1-9) |
| Aug. 18 | Elwood | L 6-28 |
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| Aug. 25 | Northeastern | L 21-25 |
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| Sep. 1 | at Hagerstown | L 12-31 |
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| Sep. 8 | Union County | L 0-28 |
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| Sep. 15 | at Cambridge City Lincoln | W 53- 0 |
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| Sep. 22 | at Union City | L 7-14 |
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| Sep. 29 | South Adams | L 14-48 |
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| Oct. 6 | at Tri | L 12-24 |
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| Oct. 13 | Centerville | L 21-22 |
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| Oct. 20 | at Indianapolis Scecina | L 18-49 |
sect |
| 1999 SEASON (7-3) |
| Aug. 20 | at Elwood | L 8-36 |
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| Aug. 27 | at Northeastern | W 44- 6 |
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| Sep. 3 | Hagerstown | W 35-28 |
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| Sep. 10 | at Union County | W 26-24 |
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| Sep. 17 | Cambridge City Lincoln | W 21-14 |
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| Sep. 24 | Union City | W 28- 6 |
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| Oct. 1 | at South Adams | L 7-35 |
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| Oct. 8 | Tri | W 7- 3 |
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| Oct. 15 | at Centerville | W 31- 7 |
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| Oct. 29 | at Indianapolis Scecina | L 13-14 |
sect |
| 1998 SEASON (3-7) |
| Aug. 21 | Pendleton Heights | L 6-49 |
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| Aug. 28 | Northeastern | W 28- 0 |
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| Sep. 4 | at Hagerstown | L 28-49 |
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| Sep. 11 | Union County | L 6-33 |
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| Sep. 18 | at Cambridge City Lincoln | L 0- 6 |
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| Sep. 25 | at Union City | L 8-40 |
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| Oct. 2 | South Adams | L 0-33 |
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| Oct. 9 | at Tri | W 34-29 |
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| Oct. 16 | Centerville | W 21- 0 |
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| Oct. 23 | Westfield | L 12-41 |
sect |
| 1997 SEASON (3-7) |
| Aug. 22 | at Pendleton Heights | L 14-70 |
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| Aug. 29 | at Northeastern | W 35- 0 |
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| Sep. 5 | Hagerstown | L 7-45 |
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| Sep. 12 | at Union County | L 6-38 |
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| Sep. 19 | Cambridge City Lincoln | L 0-34 |
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| Sep. 26 | Union City | W 45- 7 |
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| Oct. 3 | at South Adams | L 0-70 |
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| Oct. 10 | Tri | L 6-41 |
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| Oct. 17 | at Centerville | W 20- 6 |
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| Oct. 24 | at Westfield | L 6-41 |
sect |
| 1996 SEASON (3-6) |
| Aug. 24 | Northeastern | W 28- 7 |
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| Aug. 30 | at Hagerstown | L 15-20 |
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| Sep. 6 | Union County | W 41- 0 |
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| Sep. 13 | at Cambridge City Lincoln | W 69- 0 |
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| Sep. 20 | at Union City | L 0- 6 |
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| Sep. 27 | Delta | L 0-48 |
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| Oct. 4 | at Tri | L 14-36 |
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| Oct. 11 | Centerville | ot L 22-28 |
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| Oct. 18 | Tipton | L 15-18 |
sect |
| 1995 SEASON (5-4) |
| Aug. 26 | at Northeastern | W 27- 0 |
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| Sep. 1 | Hagerstown | W 13- 6 |
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| Sep. 8 | at Union County | W 39-14 |
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| Sep. 15 | Cambridge City Lincoln | W 31- 0 |
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| Sep. 22 | Union City | W 24- 8 |
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| Sep. 29 | at Delta | L 6-38 |
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| Oct. 6 | Tri | L 7-26 |
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| Oct. 13 | at Centerville | L 0-50 |
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| Oct. 20 | Westfield | L 0-26 |
sect |
| 1994 SEASON (2-7) |
| Aug. 26 | Northeastern | W 26-25 |
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| Sep. 2 | at Hagerstown | L 8-52 |
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| Sep. 9 | Union County | L 26-32 |
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| Sep. 16 | at Cambridge City Lincoln | W 27- 6 |
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| Sep. 23 | at Union City | L 6-21 |
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| Sep. 30 | Delta | L 7-49 |
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| Oct. 7 | at Tri | L 0-33 |
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| Oct. 14 | Centerville | L 13-39 |
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| Oct. 21 | at Frankton | L 14-49 |
sect |