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Dobyns-Bennett (Kingsport, TN) won their 2,000 game last year replacing Centralia, Ill. who now has a little over 1979 wins. Mt. Vernon, IL; Centralia's archrival is also in the top 5 other then that i dont know the rest P.s Centralia's name is the Centralia Orphins or the Orphin Annes so they still win the oddest name award
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These 4 were the winningest in the nation and joined Quincy for their Thanksgiving Tournament a few years ago (Centralia, IL; Collinsville, IL; Quincy, IL; & Dobyns-Bennett -Kingsport, TN).

Here are some numbers. Dobyns-Bennett comes from their own website. The Illinois teams number come from the Illiniois High School Association (IHSA) records (available online). These records are regular and postseason games but do not include tournaments, etc. I know this because the Blue Devils have 1900 some wins overall - which includes all tournament games, etc.

Dobyns-Bennett, Kingsport, TN 2064 wins - 681 losses
Centralia, IL 2028 wins - 890 losses
Collinsville, IL 1943 wins - 725 losses
Quincy Blue Devils, Quincy, IL 1743 wins - 623 losses
Mt. Vernon, IL 1733 wins - 849 losses

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