Is it possible to upload an existing Outlook calendar to SharePoint? I have a calendar with 4500+ items that is used as the primary calendar for the company, but we would like to integrate it to SharePoint if possible. From what I have researched online its only possible to "create" a new calendar in SharePoint and copy everything over. If it's possible to essentially link the existing calendar to SharePoint that would be ideal.

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It sounds like you prefer to make SharePoint "display" the outlook calendar instead of creating a new one and sync. Per my knowledge there is no OOB approach does exactly what you want. You may check for some 3rd party tools. And you can vote in userVoice here.

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