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May 2026
| South Milwaukee | Traded a 2027 10th Round Draft Pick (RCH) and Brandon Woodruff to Cheese City |
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May 2026
| Cheese City | Traded a 2027 4th Round Draft Pick (STV) to South Milwaukee |
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May 2026
| South Milwaukee | Traded a 2027 6th Round Draft Pick (RCH) and Mookie Betts to Cheese City |
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May 2026
| Cheese City | Traded a 2027 3rd Round Draft Pick (STV) to South Milwaukee |
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Mar 2026
| Brownsdale | Traded a 2026 3rd Round Draft Pick (BRA) to South Milwaukee |
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Mar 2026
| South Milwaukee | Traded Jason Adam to Brownsdale |
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Aug 2025
| South Milwaukee | Dropped Edouard Julien, Cade Povich, and Hayden Wesneski and picked up Aaron Ashby, Cody Poteet, and Jared Koenig |
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Jul 2025
| South Milwaukee | Dropped Will Brennan and picked up Mike Tauchman |
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Jun 2025
| South Milwaukee | Dropped MJ Melendez and Chase Silseth and picked up Rece Hinds and Rafael Marchan |
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Dec 2024
| Troon | Traded a 2025 10th Round Draft Pick (SCT) to South Milwaukee |
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