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| Winston Ashley |
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| Year | Host/Site | Round |
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| 1923 | Greencastle | Sectional |
| 1925 | Crawfordsville | Sectional |
| 1926 | Greencastle | Sectional |
| Martinsville | Regional |
| 1927 | Frankfort | Sectional |
| Kokomo | Regional |
| 1928 | Anderson | Sectional |
| Frankfort | Regional |
| 1929 | Logansport | Sectional |
| Rushville | Regional |
| 1930 | Marion | Sectional |
| Columbus | Regional |
| 1931 | Shelbyville | Sectional |
| Fort Wayne | Regional |
| 1932 | Indianapolis | Sectional |
| Columbus | Regional |
| Indianapolis | Finals |
| 1933 | Fort Wayne | Sectional |
| Bloomington | Regional |
| 1934 | Danville | Sectional |
| Columbus | Regional |
| 1935 | Logansport | Sectional |
| Bloomington | Regional |
| 1936 | Frankfort | Sectional |
| Fort Wayne | Regional |
| Muncie | Semistate |
| 1937 | Franklin | Sectional |
| Muncie | Regional |
| Vincennes | Semistate |
| 1938 | Muncie | Sectional |
| Greensburg | Regional |
| Vincennes | Semistate |
| 1939 | Valparaiso | Sectional |
| Marion | Regional |
| Muncie | Semistate |
| 1940 | Greencastle | Sectional |
| Fort Wayne | Regional |
| Logansport | Semistate |
| 1941 | Noblesville | Sectional |
| Attica | Regional |
| Hammond | Semistate |
| 1942 | Richmond | Sectional |
| Washington | Regional |
| Muncie | Semistate |
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