Calendar problem syncing with Microsoft Outlook

Past Apple/iCloud updates caused problem with syncing calendar on iPhone, iPad, iCloud and Microsoft Outlook. Now I have 2 calendars "Jack" and "Jack2" and the two calendars' entries are not the same. Which of the 2 calendars a new event is shown on depends on which device the new event was entered.

How do I merge these 2 calendars and in the future have only one calendar across all devices?

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