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- Oakmont Boys Basketball vs Archbishop Williams - MIAA Round of 8 - 3-10-2023
- Oakmont Boys Basketball vs Hanover - MIAA Round of 16 - 3-7-2023
- Oakmont Boys Basketball vs Greater Lowell Tech - MIAA Round of 32 - 3-3-2023
- Oakmont Girls Basketball vs Hudson - CMADA Championship 2-24-2023
- Oakmont Boys Basketball vs Worcester Tech - CMADA Championship 2-24-2023
- Oakmont Boys Basketball vs Auburn - CMADA Tournament vs Auburn 2-22-2023
- Oakmont Girls Basketball vs Quabbin - CMADA Tournament - 2-22-2023
- Oakmont Boys Basketball vs Monty Tech - CMADA Tournament - 2-20-2023
- Oakmont Girls Basketball vs Worcester Tech - CMADA Tournament - 2-20-2023
- Oakmont Boys Basketball vs Nashoba 2-13-2023
- Oakmont Boys Ice Hockey vs Lunenburg 2-11-2023
- Oakmont Girls Basketball vs Shepherd Hill 2-10-2023
- Oakmont Boys Ice Hockey vs Fitchburg 2-8-2023
- Oakmont Boys Basketball vs North Middlesex 2-7-2023
- Oakmont Girls Basketball vs Marlborough 1-31-2023
- Oakmont Boys Ice Hockey vs Assabet Valley 1-28-2023
- Oakmont Boys Basketball vs Westborough 1-27-2023
- Oakmont Boys Basketball vs Shepherd Hill 1-17-2023
- Oakmont Girls Basketball vs North Middlesex 1-13-2023
- Oakmont Girls Basketball vs Monty Tech 1-11-2023
- Oakmont Boys Basketball vs Marlborough 1-9-2023
- Oakmont Girls Basketball vs Quabbin 1-3-2023
- Oakmont Boys Ice Hockey vs Peabody 12-28-2022
- Oakmont Boys Ice Hockey vs Ludlow 12-26-2022
- Oakmont Boys Basketball vs Fitchburg 12-23-2022
- Oakmont Boys Ice Hockey vs Littleton 12-21-2022
- Oakmont Girls Basketball vs Westborough 12-20-2022
- Oakmont Boys Ice Hockey vs St. Bernard's 12-14-2022
- Oakmont Boys Ice Hockey vs Gardner 12-10-2022
- Oakmont Boys Basketball vs Quabbin 12-9-2022
- Oakmont Football vs Lunenburg Thanksgiving Day Game 11-24-2022
- Oakmont Field Hockey vs Triton - MIAA Round of 16 - 11-9-2022
- Oakmont Field Hockey vs North Middlesex - MIAA Round of 32 - 11-6-2022
- Oakmont Boys Soccer vs Bishop Stang - MIAA Round of 32 - 11-6-2022
- Oakmont Field Hockey vs Quabbin - CMADA Championship Game - 11-2-2022
- Oakmont Boys Soccer vs Blackstone Valley Tech - CMADA Championship Game 11-2-2022
- Oakmont Boys Soccer vs Keefe Tech - CMADA Semi-Finals - 10-28-2022
- Oakmont Field Hockey vs Blackstone Valley Tech 10-27-2022
- Oakmont Boys Soccer vs Auburn - CMADA Quarterfinals 10-25-2022
- Oakmont Field Hockey vs Hudson - CMADA Quarterfinals 10-25-2022
- Oakmont Boys Soccer vs Lunenburg 10-20-2022
- Oakmont Field Hockey vs Shrewsbury 10-20-2022
- Oakmont Girls Soccer vs Fitchburg 10-18-2022
- Oakmont Football vs Groton-Dunstable 10-14-2022
- Oakmont Girls Soccer vs Littleton 10-13-2022
- Oakmont Girls Soccer vs Lunenburg 10-20-2022
- Oakmont Boys Soccer vs Bromfield 10-11-2022
- Oakmont Field Hockey vs Westborough 10-7-2022
- Oakmont Boys Soccer vs Tyngsborough 10-4-2022
- Oakmont Field Hockey vs Shepherd Hill 10-3-2022