I'm no expert at this, but i would say that if you no longer have any references to your level, and it is the only thing that directly reference the enemy, then they will both be collected by the Garbage Collector as they can no longer be reached.
Im not sure if you mean 'with' or 'will', but it should happen so that when the ContentManager is Dispose'd, content is only referenced by the level/enemies (although I think the content is unusable now), then the level's reference from the main program is removed so it and all the enemies and their members/content should be collected in the next Garbage Collection. I don't think the Enemy class itself needs to dispose as disposing is meant for unmanaged resources, and the ContentManager disposes of all the unmanaged stuff it references when it is disposed.
In short I think all you need to remember is if you want something removed then unload anything from the content manager then remove the references so it is no longer attached to the Main part of the program.
However, I'm sure one of the MVP's is going to come along and tell me how wrong I am.