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- Oakmont JV Boys Basketball vs Leominster 2-19-2021
- Oakmont Varsity Boys Basketball vs Quabbin 2-17-2021
- Oakmont JV Boys Basketball vs Quabbin 2-17-2021
- Oakmont Varsity Boys Ice Hockey vs North Middlesex 2-17-2021
- Oakmont Varsity Boys Ice Hockey vs Gardner 2-15-2021
- Oakmont Girls Ice Hockey vs Leominster 2-13-2021
- Oakmont Varsity Boys Ice Hockey vs Leominster 2-13-2021
- Oakmont JV Boys Basketball vs Gardner 2-11-2021
- Oakmont Varsity Boys Basketball vs vs Gardner 2-11-2021
- Oakmont Varsity Boys Ice Hockey vs Fitchburg/Monty Tech 2-10-2021
- Oakmont Varsity Girls Basketball vs Gardner 2-8-2021
- Oakmont JV Girls Basketball vs Gardner 2-8-2021
- Oakmont Varsity Boys Ice Hockey vs Littleton 2-6-2021
- Oakmont Varsity Girls Basketball vs Leominster 2-6-2021
- Oakmont JV Girls Basketball vs Leominster 2-6-2021
- Oakmont Varsity Boys Ice Hockey vs Groton-Dunstable 2-3-2021
- Oakmont Varsity Boys Ice Hockey vs Lunenburg 1-30-2021
- Oakmont Varsity Boys Ice Hockey vs North Middlesex 1-28-2021
- Oakmont Varsity Girls Basketball vs Quabbin 1-28-2021
- Oakmont JV Girls Basketball vs Quabbin 1-28-2021
- Oakmont Varsity Boys Ice Hockey vs Gardner 1-27-2021
- Oakmont Varsity Boys Basketball vs vs Quabbin 1-25-2021
- Oakmont JV Boys Basketball vs Quabbin 1-25-2021
- Oakmont JV Girls Basketball vs Narragansett 1-18-2021
- Oakmont Varsity Girls Basketball vs Narragansett 1-18-2021
- Oakmont Varsity Boys Ice Hockey vs Groton-Dunstable 1-16-2021
- Oakmont JV Girls Basketball vs Fitchburg 1-14-2021
- Oakmont Varsity Girls Basketball vs Fitchburg 1-14-2021
- Oakmont JV Boys Basketball vs Fitchburg 1-11-2021
- Oakmont Girls Ice Hockey vs Leominster 1-13-2021
- Oakmont Boys Basketball vs Fitchburg 1-11-2021
- Oakmont Girls Ice Hockey vs Leominster 1-9-2021
- Oakmont Varsity Girls Soccer vs Quabbin 11-19-2020
- Oakmont Varsity Boys Soccer vs Quabbin 11-18-2020
- Oakmont Varsity Field Hockey vs Quabbin 11-17-2020
- Oakmont Varsity Girls Soccer vs Narragansett 10-22-2020
- Oakmont Varsity Field Hockey vs Fitchburg 10-21-2020
- Oakmont Varsity Boys Soccer vs Fitchburg 10-20-2020
- Oakmont Varsity Girls Soccer vs Quabbin 10-17-2020
- Oakmont Varsity Girls Soccer vs Gardner 10-15-2020
- Oakmont Varsity Field Hockey vs Murdock 10-12-2020
- Oakmont Varsity Boys Soccer vs Narragansett 10-8-2020
- Oakmont Varsity Girls Soccer vs Fitchburg 10-6-2020
- Oakmont Boys Basketball vs Bellingham - Quarterfinals - 2-28-2020
- Oakmont Boys Basketball vs Northbridge - MIAA Round of 32 - 2-25-2020
- Oakmont Boys Basketball vs Leominster 2-5-2020
- Oakmont Girls Basketball vs Leominster 2-5-2020
- Oakmont Boys Basketball vs Gardner 1-28-2020
- Oakmont Girls Basketball vs Gardner 1-28-2020
- Oakmont Boys Ice Hockey vs Northbridge 1-8-2020