Refueling booms with multiple couplings, and associated methods and systems, are disclosed. A system in accordance with one embodiment of the invention includes a deployable boom carrying a refueling passage. A first coupler carried by the boom can be operatively coupleable to the refueling passage. The first coupler can be configured to be releasably connected to a receiver aircraft during refueling. A second coupler can be carried by the boom and can be operatively coupleable to the refueling passage, with the second coupler being configured to be releasably connected to a receiver aircraft during refueling. In particular embodiments, the first and second couplers can have different configurations so as to be compatible with aircraft having different refueling arrangements.