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- Oakmont Varsity Football vs Maynard 10-22-2021
- Oakmont Boys Soccer vs Monty Tech 10-22-2021
- Oakmont Field Hockey vs Blackstone Valley Tech 10-22-2021
- Oakmont Boys Soccer vs Millbury 10-20-2021
- Oakmont Field Hockey vs Clinton 10-20-2021
- Oakmont Field Hockey vs North Middlesex 10-15-2021
- Oakmont Varsity Football vs Hudson 10-8-2021
- Oakmont Boys Soccer vs Fitchburg 10-14-2021
- Oakmont Boys Soccer vs Littleton 10-12-2021
- Oakmont Field Hockey vs Leominster 10-1-2021
- Oakmont Boys Soccer vs Quabbin 10-5-2021
- Oakmont Boys Soccer vs Gardner 9-27-2021
- Oakmont Girls Soccer vs Gardner 9-27-2021
- Oakmont Football vs Northbridge 9-24-2021
- Oakmont Field Hockey vs Quabbin 9-22-2021
- Oakmont Girls Soccer vs Littleton 9-21-2021
- Oakmont Field Hockey vs Westborough 9-17-2021
- Oakmont Girls Soccer vs Quabbin 9-14-2021
- Oakmont Football vs Auburn 9-10-2021
- Oakmont Varsity Baseball vs AMSA - MIAA Cenral Division 3 Finals - 6-28-2021
- Oakmont Varsity Baseball vs Northbridge - MIAA Central Division 3 Semi-Finals 6-25-2021
- Oakmont Varsity Baseball vs Uxbridge - MIAA Central Division 3 Quarterfinals - 6-23-2021
- Oakmont Varsity Baseball vs AMSA - Central Mass Division 2 Championship - 6-16-2021
- Oakmont Boys Lacrosse vs Littleton - District Quarterfinals - 6-9-2021
- Oakmont Varsity Baseball vs Blackstone Valley Tech - District Quarterfinals - 6-9-2021
- Oakmont Girls Lacrosse vs Tahanto 6-2-2021
- Oakmont Varsity Baseball vs Lunenburg 6-2-2021
- Oakmont Varsity Softball vs Lunenburg 6-2-2021
- Oakmont Boys Lacrosse vs Littleton 5-28-2021
- Oakmont Girls Lacrosse vs Lunenburg 5-25-2021
- Oakmont Boys Lacrosse vs Lunenburg 5-24-2021
- Oakmont Varsity Baseball vs Tyngsboro 5-21-2021
- Oakmont Varsity Softball vs Tyngsboro 5-21-2021
- Oakmont Boys Lacrosse vs Lunenburg 5-20-2021
- Oakmont Boys Lacrosse vs Monty Tech 5-18-2021
- Oakmont Girls Lacrosse vs Fitchburg 5-17-2021
- Oakmont Boys Lacrosse vs Hudson 5-13-2021
- Oakmont Varsity Softball vs Quabbin 5-13-2021
- Oakmont Varsity Baseball vs Quabbin 5-13-2021
- Oakmont Varsity Softball vs Littleton 5-12-2021
- Oakmont Varsity Baseball vs Littleton 5-12-2021
- Oakmont Varsity Baseball vs Clinton 5-7-2021
- Oakmont Varsity Softball vs Clinton 5-7-2021
- Oakmont Girls Lacrosse vs Hudson 5-6-2021
- Oakmont Varsity Football vs Fitchburg 4-23-2021
- Oakmont JV Football vs North Middlesex 4-19-2021
- Oakmont Varsity Football vs North Middlesex 4-18-2021
- Oakmont Varsity Football vs Nashoba 4-2-2021
- Oakmont JV Football vs Nashoba 4-1-2021
- Oakmont Varsity Boys Basketball vs Leominster 2-19-2021