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The following have been members of Softball Umpires of Maryland for Twenty (20) years.
2019 |
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| Mike Behrens, John Calamari, Jo Brickwedde, Jim Carberry | John Moore John Dye | Keith Brown |
2020 |
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2021 |
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2023 |
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| Dennis Artman, Bill Chatterton | John Remmell | Jean Little Al Palmer Dave Pabst | ||||
| 2024 |  |
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| Rick Morris, Reggie Grant, Bryan Richter |