Can the case be predicted to be likely to escalate more than one time?

Yes, the escalation prediction module will check the case details periodically during the case life; each time the module prediction factors are triggered, the Likely to Escalate tag will be added to the case, and the case will be placed in Likely to Escalate. 

You can see all the previous predictions and actions taken during reviews within the case history.

All Likely to Escalate predictions will be captured on the case timeline, and you can view the escalation key insights for each of them. 

Resources:

Escalation Manager Workflow