| Round | Date | Time | Home | Away | Venue | Field | Division | |
|---|---|---|---|---|---|---|---|---|
| R2 | Sat, Dec 6 | 8:30am | Country Day 5th/6th | vs | Stuart Hall 5th/6th | Country Day | Boys 5/6 North | |
| R3 | Tue, Dec 9 | 4:00pm | Stuart Hall 5th/6th | vs | CBS 6th | City Park Quad - Softball Complex | 5/6 | Boys 5/6 North |
| R4 | Tue, Dec 9 | 5:30pm | Trinity 6th | vs | Willow 5th/6th | LaSalle Park | 5 | Boys 5/6 North |
| R5 | Wed, Dec 10 | 6:00pm | Newman 6th | vs | Country Day 5th/6th | Country Day | Boys 5/6 North | |
| R6 | Thu, Dec 11 | 5:30pm | Newman 6th | vs | Stuart Hall 5th/6th | LaSalle Park | 6 | Boys 5/6 North |
| R7 | Sat, Dec 13 | 9:00am | Country Day 5th/6th | vs | Willow 5th/6th | Country Day | Boys 5/6 North | |
| R8 | Sat, Dec 13 | 10:30am | Holy Cross 5th/6th | vs | Trinity 6th | The Fly | 4/5 | Boys 5/6 North |
| R9 | Mon, Dec 15 | 4:00pm | CBS 6th | vs | Trinity 6th | LaSalle Park | 5 | Boys 5/6 North |
| R10 | Mon, Jan 5 | 4:00pm | Willow 5th/6th | vs | CBS 6th | LaSalle Park | 7 | Boys 5/6 North |
| R11 | Mon, Jan 5 | 6:00pm | Trinity 6th | vs | Country Day 5th/6th | The Fly | 2/3 | Boys 5/6 North |
| R13 | Thu, Jan 8 | 4:00pm | Newman 6th | vs | Willow 5th/6th | LaSalle Park | 5 | Boys 5/6 North |
| R12 | Thu, Jan 8 | 4:30pm | Holy Cross 5th/6th | vs | CBS 6th | Holy Cross | Boys 5/6 North | |
| R14 | Thu, Jan 8 | 5:30pm | Stuart Hall 5th/6th | vs | Trinity 6th | LaSalle Park | 6 | Boys 5/6 North |
| R15 | Wed, Jan 14 | 3:45pm | Stuart Hall 5th/6th | vs | Holy Cross 5th/6th | Holy Cross | Boys 5/6 North | |
| R16 | Wed, Jan 14 | 4:00pm | CBS 6th | vs | Country Day 5th/6th | Country Day | Boys 5/6 North | |
| R17 | Wed, Jan 14 | 6:00pm | Trinity 6th | vs | Newman 6th | The Fly | 2/3 | Boys 5/6 North |
| R18 | Thu, Jan 15 | 4:00pm | Willow 5th/6th | vs | Holy Cross 5th/6th | City Park Quad - Softball Complex | Boys 5/6 North | |
| R19 | Thu, Jan 15 | 5:30pm | CBS 6th | vs | Newman 6th | LaSalle Park | 6 | Boys 5/6 North |
| R20 | Sat, Jan 17 | 10:30am | Willow 5th/6th | vs | Stuart Hall 5th/6th | LaSalle Park | 5 | Boys 5/6 North |
| R21 | Sat, Jan 17 | 10:30am | Country Day 5th/6th | vs | Holy Cross 5th/6th | The Fly | 4/5 | Boys 5/6 North |
| Wed, Jan 28 | 4:00pm | Holy Cross 5th/6th | vs | Newman 6th | Holy Cross | Boys 5/6 North | ||
| QF | Mon, Feb 2 | 4:00pm | Willow 5th/6th | vs | Holy Cross 5th/6th | LaSalle Park | 6 | Boys 5/6 North |
| QF | Wed, Feb 4 | 4:00pm | Trinity 6th | vs | Stuart Hall 5th/6th | LaSalle Park | 5 | Boys 5/6 North |
| QF | Wed, Feb 4 | 7:00pm | CBS 6th | vs | Country Day 5th/6th | Country Day | 6 | Boys 5/6 North |
| SF | Thu, Feb 5 | 6:00pm | Newman 6th | vs | Holy Cross 5th/6th | Holy Cross | Boys 5/6 North | |
| SF | Fri, Feb 6 | 4:00pm | Country Day 5th/6th | vs | Stuart Hall 5th/6th | LaSalle Park | 7 | Boys 5/6 North |
| FINAL | Mon, Feb 9 | 4:00pm | Newman 6th | vs | Stuart Hall 5th/6th | LaSalle Park | 7 | Boys 5/6 North |