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Thu, 23 Oct 2025 | 7:45 PM Z |
 Polytech High School vs Middletown High School  |
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Mon, 13 Oct 2025 | 10:15 PM Z |
 St. Georges Technical High School vs Middletown High School |
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Mon, 29 Sep 2025 | 7:45 PM Z |
 Away vs Middletown High School |
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Fri, 26 Sep 2025 | 7:45 PM Z |
 Delaware Military Academy vs Middletown High School |
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Wed, 24 Sep 2025 | 10:15 PM Z |
 Appoquinimink High School vs Middletown High School |
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Thu, 18 Sep 2025 | 10:15 PM Z |
 Caesar Rodney High School vs Middletown High School |
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Thu, 18 Sep 2025 | 9:00 PM Z |
Caesar Rodney High School vs Middletown High School |
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Mon, 15 Sep 2025 | 9:00 PM Z |
 Delcastle Vo-Tech High School vs Middletown High School |
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Mon, 15 Sep 2025 | 7:45 PM Z |
Delcastle Vo-Tech High School vs Middletown High School |
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Fri, 5 Sep 2025 | 7:45 PM Z |
 Dover High School vs Middletown High School |
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Thu, 1 May 2025 | 11:00 PM Z |
Middletown High School vs Oakdale High School  |
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Thu, 1 May 2025 | 9:30 PM Z |
Middletown High School vs Oakdale High School |
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Mon, 28 Apr 2025 | 11:00 PM Z |
 Smithsburg High School vs Middletown High School |
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Mon, 28 Apr 2025 | 9:30 PM Z |
Smithsburg High School vs Middletown High School |
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Thu, 24 Apr 2025 | 11:00 PM Z |
Middletown High School vs Gov Thomas Johnson High School  |
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Tue, 22 Apr 2025 | 11:00 PM Z |
Middletown High School vs Catoctin High School  |
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Tue, 22 Apr 2025 | 11:00 PM Z |
Catoctin High School vs Middletown High School |
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Tue, 22 Apr 2025 | 9:30 PM Z |
Catoctin High School vs Middletown High School |
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Tue, 15 Apr 2025 | 11:00 PM Z |
 Frederick High School vs Middletown High School |
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Tue, 15 Apr 2025 | 9:30 PM Z |
Frederick High School vs Middletown High School |
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Thu, 10 Apr 2025 | 11:00 PM Z |
 Boonsboro High School vs Middletown High School |
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Thu, 10 Apr 2025 | 9:30 PM Z |
Boonsboro High School vs Middletown High School |
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Tue, 8 Apr 2025 | 11:00 PM Z |
 Brunswick High School vs Middletown High School |
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Tue, 8 Apr 2025 | 9:30 PM Z |
Middletown High School vs Brunswick High School |
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Tue, 8 Apr 2025 | 9:30 PM Z |
Middletown High School vs Brunswick High School |
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Tue, 8 Apr 2025 | 9:30 PM Z |
Brunswick High School vs Middletown High School |
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Mon, 7 Apr 2025 | 11:00 PM Z |
Middletown High School vs Frederick High School |
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Mon, 7 Apr 2025 | 9:30 PM Z |
Middletown High School vs Frederick High School |
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Fri, 4 Apr 2025 | 8:00 PM Z |
Middletown High School vs Francis Scott Key High School  |
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Thu, 3 Apr 2025 | 11:00 PM Z |
 Walkersville High School vs Middletown High School |
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