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Dear IBN.,
We are glad to help you and we may need some more information for confirmation.
From the description, I think that the SharePoint calendar is the Microsoft 365 group calendar as there is no SharePoint calendar in Outlook. In Outlook, there are the shared calendar from a shared mailbox, the user's default calendar, the calendar imported from Planner and the Microsoft 365 group calendar.
In SharePoint Online, there is only the classic calendar list or the list with the modern calendar view.
So could you confirm whether you mean a Microsoft 365 group calendar in your environment or a classic calendar list like the following?
As the Microsoft 365 group calendar is a part in the Microsoft 365 group in Exchange Online, it should be an Exchange issue. If you are using the Microsoft 365 group calendar, in your first screenshots, I see that the default calendar is also checked. About the issue, do you mean that you can't see the group listed in Outlook and can't see the group calendar or you can't see the upcoming events in the group calendar?
Is the second screenshots showing all events in the affected group calendar?
If yes, could you uncheck the Default calendar tab and only check the affected group calendar tab to see and let us know the result?
Welcome to share any updates at your convenience.
Your effort and time are greatly appreciated!
Sincerely
Cliff | Microsoft Community Moderator