| Time | Home | Away | Location |
| Sunday, August 09 | |
| 10:00 AM | Pitch Slappers (1) | Classic Rewinds (0) | Green Acres (Softball) |
| 11:00 AM | Empty Pitchers (21) | JCL (1) | Green Acres (Softball) |
| 12:00 PM | Benchwarmers (0) | Bombers (1) | Green Acres (Softball) |
| 1:00 PM | JoBu's Refills (8) | O'Crew (16) | Green Acres (Softball) |
| 2:00 PM | Dirtbags (11) | Blackouts (12) | Green Acres (Softball) |
| 3:00 PM | Cheap Dates (9) | Green Street Elite (10) | Green Acres (Softball) |
| 4:00 PM | The Chuggers (14) | Dorn's Matadors (6) | Green Acres (Softball) |
| 5:00 PM | Amherst All Stars (8) | The Swinging Richards (15) | Green Acres (Softball) |
| 6:00 PM | The Franchise (17) | The Shockers (1) | Green Acres (Softball) |
| Sunday, August 16 | |
| 12:00 PM | Super Man That Throw (22) | Bombers (23) | Derryfield West |
| 1:00 PM | Cheap Dates (14) | Classic Rewinds (9) | St. Anthony (South) |
| 1:15 PM | Empty Pitchers (23) | O'Crew (5) | Derryfield West |
| 2:30 PM | Benchwarmers (15) | Blackouts (14) | Derryfield West |
| 3:30 PM | The Chuggers (23) | The Shockers (1) | St. Anthony (South) |
| 3:45 PM | JoBu's Refills (10) | Green Street Elite (11) | Derryfield West |
| 4:45 PM | Amherst All Stars (8) | The Franchise (17) | St. Anthony (South) |
| 5:00 PM | Dirtbags (8) | Dorn's Matadors (5) | Derryfield West |
| 6:00 PM | JCL (13) | Baked Clams (21) | St. Anthony (South) |
| Sunday, August 23 | |
| 12:00 PM | JCL (11) | O'Crew (8) | Derryfield West |
| 1:00 PM | JoBu's Refills (18) | Dorn's Matadors (8) | St. Anthony (South) |
| 1:15 PM | Benchwarmers (25) | Classic Rewinds (13) | Derryfield West |
| 2:15 PM | Cheap Dates (4) | The Shockers (5) | St. Anthony (South) |
| 2:30 PM | Empty Pitchers (9) | Green Street Elite (11) | Derryfield West |
| 3:30 PM | Pitch Slappers (0) | The Franchise (13) | St. Anthony (South) |
| 4:45 PM | The Chuggers (33) | Amherst All Stars (6) | St. Anthony (South) |
| 6:00 PM | Dirtbags (6) | The Swinging Richards (12) | St. Anthony (South) |
| Sunday, August 30 | |
| 11:00 AM | Bombers (6) | Blackouts (18) | Derryfield East |
| 12:15 PM | JCL (12) | Green Street Elite (24) | Derryfield East |
| 1:00 PM | Dirtbags (5) | The Franchise (19) | St. Anthony (South) |
| 1:30 PM | Super Man That Throw (23) | Classic Rewinds (1) | Derryfield East |
| 2:15 PM | JoBu's Refills (18) | The Shockers (11) | St. Anthony (South) |
| 2:45 PM | Empty Pitchers (12) | Dorn's Matadors (7) | Derryfield East |
| 3:30 PM | Pitch Slappers (0) | The Chuggers (1) | St. Anthony (South) |
| 4:00 PM | Benchwarmers (9) | The Swinging Richards (17) | Derryfield East |
| 4:45 PM | O'Crew (17) | Baked Clams (10) | St. Anthony (South) |
| 6:00 PM | Cheap Dates (16) | Amherst All Stars (17) | St. Anthony (South) |
| Sunday, September 13 | |
| 11:00 AM | JoBu's Refills (17) | Amherst All Stars (4) | Derryfield West |
| 12:15 PM | Dirtbags (3) | The Chuggers (21) | Derryfield West |
| 1:00 PM | O'Crew (4) | Green Street Elite (14) | Derryfield East |
| 1:30 PM | Cheap Dates (20) | Pitch Slappers (6) | Derryfield West |
| 2:15 PM | Bombers (15) | Classic Rewinds (10) | Derryfield East |
| 2:45 PM | Baked Clams (10) | Blackouts (8) | Derryfield West |
| 3:30 PM | JCL (7) | Dorn's Matadors (4) | Derryfield East |
| 4:00 PM | Benchwarmers (0) | The Franchise (5) | Derryfield West |
| 4:45 PM | Super Man That Throw (2) | The Swinging Richards (10) | Derryfield East |
| 5:15 PM | Empty Pitchers (15) | The Shockers (3) | Derryfield West |
| Sunday, September 20 | |
| 11:00 AM | Benchwarmers (19) | The Chuggers (20) | Derryfield West |
| 12:15 PM | JoBu's Refills (7) | Pitch Slappers (3) | Derryfield West |
| 1:00 PM | Blackouts (16) | Classic Rewinds (4) | Green Acres (Softball) |
| 1:30 PM | Dirtbags (12) | Cheap Dates (6) | Derryfield West |
| 2:15 PM | O'Crew (11) | Dorn's Matadors (3) | Green Acres (Softball) |
| 2:45 PM | Green Street Elite (19) | Baked Clams (13) | Derryfield West |
| 3:30 PM | Bombers (4) | The Swinging Richards (18) | Green Acres (Softball) |
| 4:00 PM | Empty Pitchers (24) | Amherst All Stars (14) | Derryfield West |
| 4:45 PM | JCL (1) | The Shockers (0) | Green Acres (Softball) |
| 5:15 PM | Super Man That Throw (5) | The Franchise (20) | Derryfield West |
| Sunday, September 27 | |
| 11:00 AM | Green Street Elite (29) | Dorn's Matadors (5) | Derryfield West |
| 12:15 PM | Blackouts (0) | The Swinging Richards (1) | Derryfield West |
| 1:00 PM | JCL (1) | Amherst All Stars (0) | Green Acres (Softball) |
| 1:30 PM | O'Crew (1) | The Shockers (0) | Derryfield West |
| 2:15 PM | JoBu's Refills (2) | Dirtbags (11) | Green Acres (Softball) |
| 2:45 PM | Bombers (11) | The Franchise (13) | Derryfield West |
| 3:30 PM | Benchwarmers (14) | Cheap Dates (15) | Green Acres (Softball) |
| 4:00 PM | Super Man That Throw (6) | The Chuggers (14) | Derryfield West |
| 4:45 PM | Baked Clams (13) | Classic Rewinds (9) | Green Acres (Softball) |
| 5:15 PM | Empty Pitchers (1) | Pitch Slappers (0) | Derryfield West |
| Sunday, October 04 | |
| 10:00 AM | Classic Rewinds (3) | The Swinging Richards (21) | Green Acres (Softball) |
| 11:00 AM | Green Street Elite (9) | The Shockers (5) | Green Acres (Softball) |
| 12:00 PM | Blackouts (8) | The Franchise (14) | Green Acres (Softball) |
| 1:00 PM | Benchwarmers (11) | JoBu's Refills (9) | Green Acres (Softball) |
| 2:00 PM | JCL (17) | Pitch Slappers (10) | Green Acres (Softball) |
| 3:00 PM | Super Man That Throw (0) | Cheap Dates (1) | Green Acres (Softball) |
| 4:00 PM | Bombers (3) | The Chuggers (10) | Green Acres (Softball) |
| 5:00 PM | Dorn's Matadors (11) | Baked Clams (16) | Green Acres (Softball) |
| Sunday, October 11 | |
| 11:00 AM | Baked Clams (24) | Super Man That Throw (10) | Derryfield West |
| 11:00 AM | O'Crew (15) | Amherst All Stars (11) | Derryfield East |
| 12:15 PM | Baked Clams (31) | Bombers (12) | Derryfield West |
| 12:15 PM | Empty Pitchers (7) | Dirtbags (6) | Derryfield East |
| 1:30 PM | Pitch Slappers (10) | The Swinging Richards (15) | Derryfield East |
| 1:30 PM | Super Man That Throw (18) | Blackouts (19) | Derryfield West |
| Sunday, October 18 | |
11:00 AM
Playoff | The Swinging Richards (20) | Baked Clams (13) | Derryfield West |
11:00 AM
Playoff | The Chuggers (13) | Empty Pitchers (20) | Derryfield East |
12:15 PM
Playoff | Green Street Elite (16) | O'Crew (1) | Derryfield West |
12:15 PM
Playoff | The Franchise (16) | JCL (10) | Derryfield East |
1:30 PM
Playoff | The Franchise (6) | The Swinging Richards (5) | Derryfield West |
1:30 PM
Playoff | Green Street Elite (6) | Empty Pitchers (11) | Derryfield East |
2:45 PM
Championship | The Franchise (8) | Empty Pitchers (9) | Derryfield West |