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| CHESTERTON |
| 2008 SEASON (9-3) |
| Aug. 22 | South Bend Clay | W 34- 6 |
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| Aug. 29 | at West Ottawa (Mich.) | L 7-28 |
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| Sep. 5 | Michigan City | W 33-21 |
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| Sep. 12 | at LaPorte | W 25-13 |
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| Sep. 19 | at Valparaiso | W 12-10 |
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| Sep. 26 | Portage | W 37-14 |
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| Oct. 3 | at Lake Central | W 28-10 |
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| Oct. 10 | at Crown Point | W 20- 7 |
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| Oct. 17 | Merrillville | L 14-28 |
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| Oct. 24 | Michigan City | W 28-19 |
sect |
| Oct. 31 | at Valparaiso | W 10- 6 |
sect |
| Nov. 7 | Merrillville | L 7-14 |
sect |
| 2007 SEASON (6-4) |
| Aug. 17 | at South Bend Clay | W 27-20 |
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| Aug. 25 | West Ottawa (Mich.) | W 42-28 |
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| Aug. 31 | at Michigan City | W 22-20 |
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| Sep. 7 | LaPorte | W 22-20 |
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| Sep. 14 | Valparaiso | L 20-28 |
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| Sep. 21 | at Portage | W 14- 7 |
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| Sep. 28 | Lake Central | W 31-24 |
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| Oct. 5 | Crown Point | L 24-42 |
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| Oct. 12 | at Merrillville | L 10-38 |
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| Oct. 19 | Merrillville | L 0-21 |
sect |
| 2006 SEASON (5-6) |
| Aug. 18 | Andrean | L 16-22 |
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| Aug. 25 | at Griffith | ot L 34-35 |
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| Sep. 1 | Michigan City | W 49-14 |
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| Sep. 8 | at LaPorte | L 21-34 |
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| Sep. 15 | at Valparaiso | W 33-21 |
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| Sep. 22 | Portage | ot L 3- 6 |
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| Sep. 29 | at Lake Central | W 63-36 |
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| Oct. 6 | at Crown Point | L 21-41 |
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| Oct. 13 | Merrillville | W 22-13 |
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| Oct. 20 | at Michigan City | W 18- 6 |
sect |
| Oct. 27 | Merrillville | L 22-39 |
sect |
| 2005 SEASON (3-8) |
| Aug. 19 | at Andrean | L 14-17 |
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| Aug. 26 | Griffith | L 7-56 |
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| Sep. 2 | at Michigan City | L 35-49 |
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| Sep. 9 | LaPorte | L 27-38 |
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| Sep. 16 | Valparaiso | L 21-35 |
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| Sep. 23 | at Portage | W 28-14 |
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| Sep. 30 | Lake Central | W 31- 6 |
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| Oct. 7 | Crown Point | L 17-34 |
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| Oct. 14 | at Merrillville | L 23-35 |
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| Oct. 21 | Portage | W 49-28 |
sect |
| Oct. 28 | at Crown Point | L 0-34 |
sect |
| 2004 SEASON (5-5) |
| Aug. 20 | Andrean | L 13-18 |
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| Aug. 27 | at Griffith | W 34-21 |
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| Sep. 3 | Michigan City | W 48- 0 |
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| Sep. 10 | at LaPorte | W 21-14 |
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| Sep. 17 | at Valparaiso | L 14-31 |
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| Sep. 24 | Portage | W 35-19 |
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| Oct. 1 | at Lake Central | W 42-14 |
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| Oct. 8 | at Crown Point | L 14-17 |
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| Oct. 15 | Merrillville | L 17-20 |
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| Oct. 22 | Portage | L 28-35 |
sect |
| 2003 SEASON (7-4) |
| Aug. 22 | at Andrean | L 7-21 |
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| Aug. 29 | Griffith | W 32-20 |
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| Sep. 5 | at Michigan City | W 32- 7 |
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| Sep. 12 | LaPorte | W 42-23 |
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| Sep. 19 | Valparaiso | W 42-14 |
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| Sep. 26 | at Portage | L 19-21 |
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| Oct. 3 | Lake Central | W 45- 7 |
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| Oct. 10 | Crown Point | W 33-14 |
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| Oct. 17 | at Merrillville | L 3- 7 |
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| Oct. 24 | Michigan City | W 16-12 |
sect |
| Oct. 31 | at Merrillville | L 14-21 |
sect |
| 2002 SEASON (6-4) |
| Aug. 23 | Highland | W 34- 3 |
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| Aug. 30 | Mishawaka | W 17- 6 |
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| Sep. 6 | Michigan City | W 42- 0 |
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| Sep. 13 | at LaPorte | otW 21-20 |
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| Sep. 20 | at Valparaiso | L 10-17 |
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| Sep. 27 | Portage | W 42-40 |
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| Oct. 4 | at Hobart | W 33-13 |
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| Oct. 11 | at Crown Point | L 21-35 |
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| Oct. 18 | Merrillville | L 12-36 |
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| Oct. 25 | at Crown Point | L 14-34 |
sect |
| 2001 SEASON (6-6) |
| Aug. 17 | Hammond Noll | W 31- 0 |
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| Aug. 24 | at Mishawaka | L 10-35 |
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| Aug. 31 | at Michigan City | W 21- 7 |
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| Sep. 7 | LaPorte | L 3-10 |
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| Sep. 14 | Valparaiso | L 7-39 |
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| Sep. 21 | at Portage | L 14-41 |
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| Sep. 28 | Hobart | W 17-15 |
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| Oct. 5 | Crown Point | W 14- 0 |
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| Oct. 12 | at Merrillville | L 3-13 |
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| Oct. 19 | Crown Point | W 35- 7 |
sect |
| Oct. 26 | at Merrillville | W 19- 6 |
sect |
| Nov. 2 | at Valparaiso | L 14-42 |
sect |
| 2000 SEASON (8-2) |
| Aug. 18 | at Hammond Noll | W 54- 0 |
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| Aug. 25 | Northridge | W 37- 6 |
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| Sep. 1 | Michigan City | W 34-12 |
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| Sep. 8 | at LaPorte | W 32-15 |
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| Sep. 15 | at Valparaiso | W 17-14 |
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| Sep. 22 | Portage | W 17- 7 |
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| Sep. 29 | at Hobart | L 13-41 |
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| Oct. 6 | at Crown Point | W 28-14 |
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| Oct. 13 | Merrillville | W 26- 7 |
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| Oct. 20 | East Chicago Central | L 21-28 |
sect |
| 1999 SEASON (7-3) |
| Aug. 20 | Hammond Noll | W 36-19 |
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| Aug. 27 | at Northridge | W 41- 7 |
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| Sep. 3 | at Michigan City | W 38- 7 |
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| Sep. 10 | LaPorte | W 28-20 |
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| Sep. 17 | Valparaiso | W 47-21 |
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| Sep. 24 | at Portage | L 10-27 |
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| Oct. 1 | Hobart | W 45-16 |
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| Oct. 8 | Crown Point | W 56-28 |
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| Oct. 15 | at Merrillville | ot L 35-42 |
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| Oct. 22 | at Valparaiso | L 17-21 |
sect |
| 1998 SEASON (5-6) |
| Aug. 21 | at Hammond Noll | L 17-23 |
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| Aug. 28 | Northridge | W 7- 0 |
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| Sep. 4 | Michigan City | W 21-13 |
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| Sep. 11 | at LaPorte | W 24-13 |
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| Sep. 18 | at Valparaiso | L 14-44 |
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| Sep. 25 | Portage | L 10-21 |
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| Oct. 2 | at Hobart | L 7-14 |
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| Oct. 9 | at Crown Point | L 17-24 |
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| Oct. 16 | Merrillville | W 24-14 |
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| Oct. 23 | at South Bend Riley | W 21-15 |
sect |
| Oct. 30 | at Penn | L 21-42 |
sect |
| 1997 SEASON (3-7) |
| Aug. 22 | Hammond Noll | W 35- 0 |
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| Aug. 29 | at Andrean | L 0-14 |
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| Sep. 5 | at Michigan City | W 14- 9 |
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| Sep. 12 | LaPorte | 2otW 16-10 |
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| Sep. 19 | Valparaiso | L 7-27 |
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| Sep. 26 | at Portage | L 6-38 |
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| Oct. 3 | Hobart | L 3-28 |
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| Oct. 10 | Crown Point | L 14-20 |
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| Oct. 17 | at Merrillville | L 14-40 |
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| Oct. 24 | Penn | L 10-42 |
sect |
| 1996 SEASON (6-5) |
| Aug. 23 | Andrean | W 41-10 |
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| Aug. 30 | Merrillville | L 10-44 |
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| Sep. 6 | at LaPorte | W 11- 7 |
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| Sep. 13 | at Valparaiso | W 17-10 |
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| Sep. 20 | at Hobart | L 0-56 |
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| Sep. 27 | Michigan City | W 15-13 |
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| Oct. 4 | at Crown Point | L 33-35 |
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| Oct. 11 | Portage | L 14-17 |
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| Oct. 18 | at Michigan City | W 31- 0 |
sect |
| Oct. 25 | Elkhart Central | W 21-14 |
sect |
| Nov. 1 | at Penn | L 14-41 |
sect |
| 1995 SEASON (3-7) |
| Aug. 26 | (n)Andrean | W 33-27 |
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| Sep. 1 | at Merrillville | L 7-34 |
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| Sep. 8 | LaPorte | W 10- 7 |
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| Sep. 15 | Valparaiso | L 28-45 |
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| Sep. 22 | Hobart | L 14-47 |
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| Sep. 29 | at Michigan City | L 17-28 |
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| Oct. 6 | Crown Point | L 7-24 |
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| Oct. 13 | at Portage | L 7-39 |
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| Oct. 20 | at Warsaw | W 13- 0 |
sect |
| Oct. 27 | Michigan City | L 14-20 |
sect |
| 1994 SEASON (3-6) |
| Aug. 26 | Andrean | W 20- 6 |
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| Sep. 2 | Merrillville | L 7-35 |
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| Sep. 9 | at LaPorte | L 23-34 |
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| Sep. 16 | at Valparaiso | L 21-28 |
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| Sep. 23 | at Hobart | L 13-55 |
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| Sep. 30 | M.C. Rogers | W 38- 8 |
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| Oct. 7 | at Crown Point | 2otW 35-34 |
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| Oct. 14 | Portage | L 7-41 |
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| Oct. 21 | at Valparaiso | L 3-21 |
sect |