| 09/10/2023 | Northeast Whalers-B2015-Morrison | Metro Beacons Blue-B2015-Silvestri | 12:00PM - 1:15PM | Iron Rail- Wenham Mass. / 7A |
| 09/10/2023 | North Central Spirit Blue-B2014-Liotta | Metro Beacons Blue-B2014-Ivan Silva | 1:00PM - 2:15PM | Mass Youth Soccer Complex / 16B |
| 09/10/2023 | Northeast Whalers-B2014-Tom Silva | Metro Beacons Red-B2014-Marable | 1:30PM - 2:45PM | Iron Rail- Wenham Mass. / 7A |
| 09/15/2023 | North Central Spirit-B2015-Caissey | Metro Beacons Red-B2015-Abozaid | 6:00PM - 7:15PM | Mass Youth Soccer Complex / 16B |
| 09/15/2023 | North Central Spirit Red-B2014-Burke | North Central Spirit White-B2014-St. Germain | 6:00PM - 7:15PM | Mass Youth Soccer Complex / 16C |
| 09/24/2023 | Metro Beacons Blue-B2014-Ivan Silva | Northeast Whalers-B2014-Tom Silva | 12:00PM - 1:15PM | Iron Rail- Wenham Mass. / 7A |
| 09/24/2023 | North Central Spirit-B2015-Caissey | Northeast Whalers-B2015-Morrison | 12:00PM - 1:15PM | Mass Youth Soccer Complex / 16B |
| 09/24/2023 | Metro Beacons Red-B2015-Abozaid | Metro Beacons Blue-B2015-Silvestri | 1:30PM - 2:45PM | Iron Rail- Wenham Mass. / 7A |
| 09/24/2023 | North Central Spirit White-B2014-St. Germain | North Central Spirit Blue-B2014-Liotta | 1:30PM - 2:45PM | Mass Youth Soccer Complex / 16B |
| 09/24/2023 | Metro Beacons Red-B2014-Marable | North Central Spirit Red-B2014-Burke | 3:00PM - 4:15PM | Mass Youth Soccer Complex / 16B |
| 10/15/2023 | Metro Beacons Blue-B2015-Silvestri | North Central Spirit-B2015-Caissey | 12:00PM - 1:15PM | Iron Rail- Wenham Mass. / 7A |
| 10/15/2023 | Northeast Whalers-B2015-Morrison | Metro Beacons Red-B2015-Abozaid | 12:00PM - 1:15PM | Iron Rail- Wenham Mass. / 7B |
| 10/15/2023 | North Central Spirit Red-B2014-Burke | Metro Beacons Blue-B2014-Ivan Silva | 1:30PM - 2:45PM | Iron Rail- Wenham Mass. / 7A |
| 10/15/2023 | Northeast Whalers-B2014-Tom Silva | North Central Spirit Blue-B2014-Liotta | 1:30PM - 2:45PM | Iron Rail- Wenham Mass. / 7B |
| 10/15/2023 | Metro Beacons Red-B2014-Marable | North Central Spirit White-B2014-St. Germain | 3:00PM - 4:15PM | Iron Rail- Wenham Mass. / 7A |
| 10/29/2023 | Metro Beacons Blue-B2014-Ivan Silva | Metro Beacons Red-B2014-Marable | 1:00PM - 2:15PM | Mass Youth Soccer Complex / 16B |
| 10/29/2023 | North Central Spirit White-B2014-St. Germain | Northeast Whalers-B2014-Tom Silva | 2:30PM - 3:45PM | Mass Youth Soccer Complex / 16B |
| 10/29/2023 | Metro Beacons Blue-B2015-Silvestri | Northeast Whalers-B2015-Morrison | 3:00PM - 4:15PM | Iron Rail- Wenham Mass. / 7A |
| 10/29/2023 | Metro Beacons Red-B2015-Abozaid | North Central Spirit-B2015-Caissey | 3:30PM - 4:45PM | Mass Youth Soccer Complex / 16A |
| 10/29/2023 | North Central Spirit Blue-B2014-Liotta | North Central Spirit Red-B2014-Burke | 4:00PM - 5:15PM | Mass Youth Soccer Complex / 16B |