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| April | May | June | July | August | Playoffs |
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| May |
| Friday, May 5, 2023 | 6:00:00 PM Southside Tavern at Shamrock Pub
7:30:00 PM The Greatest Bar at La Familia
9:00:00 PM PowTown at Shannon Tavern
| | Monday, May 8, 2023 | 6:00:00 PM Pat Simpson Club at Playwright Shamrocks
7:30:00 PM Stew Jays at MarineMax Boston
9:00:00 PM Broadway Brew Crew at Big Ballers
| | Tuesday, May 9, 2023 | 6:00:00 PM Publico at Fauci's Frozen Ropes
7:30:00 PM STATS Sluggers at SLS
9:00:00 PM MJS Braves at Silkworms
| | Wednesday, May 10, 2023 | 6:00:00 PM Broadway Brew Crew at Stew Jays
7:45:00 PM Dirty Fungos at Seapoint Slammers
9:00:00 PM Southside Tavern at Shannon Tavern
| | Thursday, May 11, 2023 | 6:00:00 PM Silkworms at Loco Pirates
7:30:00 PM The Spot Clothing at Roza Lyons
9:00:00 PM DRT at Fat Baby
| | Friday, May 12, 2023 | 6:00:00 PM MarineMax Boston at Seapoint Slammers
7:30:00 PM Fauci's Frozen Ropes at STATS Sluggers
9:00:00 PM Lincoln Tavern at L Street Tavern
| | Monday, May 15, 2023 | 6:00:00 PM Fat Baby at The Greatest Bar
6:00:01 PM Roza Lyons at La Familia N Street
7:30:00 PM Loco Pirates at DRT
7:30:01 PM Publico at The Spot Clothing N Street
9:00:00 PM Fauci's Frozen Ropes at Telegraph Hill
9:00:01 PM SLS at MJS Braves N Street
| | Tuesday, May 16, 2023 | 6:00:00 PM Big Ballers at Playwright Shamrocks
7:30:00 PM Shannon Tavern at Lincoln Tavern
9:00:00 PM Dirty Fungos at Pat Simpson Club
| | Wednesday, May 17, 2023 | 6:00:00 PM Silkworms at STATS Sluggers
7:30:00 PM Shamrock Pub at Lincoln Tavern
9:00:00 PM Seapoint Slammers at PowTown
| | Thursday, May 18, 2023 | 6:00:00 PM L Street Tavern at Stew Jays
7:30:00 PM Broadway Brew Crew at Southside Tavern
9:00:00 PM Shamrock Pub at MarineMax Boston
| | Friday, May 19, 2023 | 6:00:00 PM Seapoint Slammers at Pat Simpson Club
6:00:01 PM PowTown at Dirty Fungos N Street
7:30:00 PM Fat Baby at Telegraph Hill
7:30:01 PM Playwright Shamrocks at Broadway Brew Crew N Street
9:00:01 PM The Spot Clothing at Loco Pirates N Street
| | Monday, May 22, 2023 | 6:00:00 PM MJS Braves at Telegraph Hill
6:00:01 PM Fat Baby at SLS N Street
7:30:00 PM Loco Pirates at La Familia
7:30:01 PM Southside Tavern at Pat Simpson Club N Street
9:00:00 PM The Greatest Bar at Silkworms
9:00:01 PM STATS Sluggers at DRT N Street
| | Tuesday, May 23, 2023 | 6:00:00 PM Shamrock Pub at Shannon Tavern
7:30:00 PM Fauci's Frozen Ropes at The Spot Clothing
9:00:00 PM Playwright Shamrocks at Lincoln Tavern
| | Wednesday, May 24, 2023 | 6:00:00 PM DRT at The Spot Clothing
6:00:01 PM Roza Lyons at The Greatest Bar N Street
7:30:00 PM MJS Braves at STATS Sluggers
7:30:01 PM Fauci's Frozen Ropes at Silkworms N Street
9:00:00 PM SLS at Publico
9:00:01 PM La Familia at Big Ballers N Street
| | Thursday, May 25, 2023 | 6:00:00 PM Telegraph Hill at Publico
6:00:01 PM Lincoln Tavern at MarineMax Boston N Street
7:30:00 PM Big Ballers at L Street Tavern
7:30:01 PM Stew Jays at PowTown N Street
9:00:00 PM Dirty Fungos at Broadway Brew Crew
9:00:01 PM Seapoint Slammers at Shamrock Pub N Street
| | Tuesday, May 30, 2023 | 6:00:00 PM PowTown at Lincoln Tavern
7:30:00 PM Shannon Tavern at Playwright Shamrocks
9:00:00 PM Pat Simpson Club at Stew Jays
| | Wednesday, May 31, 2023 | 6:00:00 PM The Spot Clothing at STATS Sluggers
7:30:00 PM DRT at Telegraph Hill
9:00:00 PM La Familia at Silkworms
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