The present disclosure relates to generating and utilizing digital associations between digital documents and digital calendar events based on determined content connections. For example, one or more embodiments suggest a digital document to a user for association with a digital calendar event based on content connections between the digital document and the digital calendar event. In particular, one or more embodiments determine a content connection based on document characteristics (e.g., document content and access characteristics) and calendar event characteristics (e.g., calendar content and historical meeting information). For example, the system can train a machine learning model to determine content connections based on document characteristics and calendar event characteristics. By associating digital documents with digital calendar events, the system can efficiently manage digital documents for participants, automatically generate new digital documents for calendar events, generate snippets for insertion within digital documents, and generate calendar event summaries and action items.