Thanks for the file. It works here.
Some pointers: The Cloth is dependent on the medal Dynamics. So caching the medal movement first might help.
Besides, instead of using the “build-in” cache, use the Object Manager> Tags> Rigging Tags> Point Cache.
When the point cache is working, you might disable the dynamic-based tags not to get twice the input.
Start with the medal first, then anything else. There is a hierarchy in the motion. Typically it is best to understand the hierarchy and sort the object manager as much as possible (top [first] to bottom [last])
I hope that makes sense.
I’m offline now. It’s past midnight here.
All the best