Wiremock: Multiple responses for the same URL and content?

This is what the Scenarios feature is for.

You’ll need to put both stubs into a scenario (i.e. same scenario name), make the first stub trigger a transition to a new state, then make the second stub contingent on the scenario being in the second state and the first stub contingent on the scenario being in the STARTED state.

See: http://wiremock.org/docs/stateful-behaviour/