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Kevin O'Leary Career Regular Season | Career Post Season Career Batting | Career Pitching | Career Fielding |
By League |
| Season | Team | G | PO | A | E | FPC | |
| 2010 Boston American MSBL | Weymouth Grays | 15 | 0 | 1 | 1 | .500 | |
| 2011 Boston American MSBL | Weymouth Grays | 17 | 0 | 0 | 0 | .000 | |
| 2012 Boston American MSBL | Weymouth Grays | 17 | 2 | 5 | 2 | .778 | |
| 2014 Boston Masters MSBL | South Shore Giants | 12 | 0 | 0 | 6 | .000 | |
| 2015 Boston Masters MSBL | South Shore Giants | 15 | 0 | 1 | 4 | .200 | |
| 2016 Boston MSBL Masters | South Shore Giants | 17 | 0 | 1 | 4 | .200 | |
| 2017 Boston MSBL Masters | South Shore Giants | 10 | 0 | 0 | 4 | .000 | |
| 2018 Boston MSBL Masters | South Shore Giants | 12 | 0 | 0 | 0 | .000 | |
| 2019 Boston MSBL Masters | South Shore Giants | 14 | 0 | 0 | 0 | .000 | |
| 2020 Boston MSBL Masters | South Shore Giants | 1 | 0 | 0 | 0 | .000 | |
| 2021 Boston MSBL Masters | South Shore Giants | 4 | 0 | 0 | 0 | .000 | |
| 2022 Boston Masters | South Shore Giants | 5 | 0 | 0 | 0 | .000 | |
| 2023 Boston Masters | South Shore Mariners | 3 | 0 | 0 | 0 | .000 | |
| Totals | 142 | 2 | 8 | 21 | .323 |
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