An air maintenance tire and air pump assembly is provided including a tire and an elongate tubular air passageway enclosed within a flexing region of a tire sidewall. A plurality of check valve devices are spaced apart and positioned along the air passageway into multiple air passageway segments. A check valve membrane opens to allow pressurized air to directionally pass through the check valve device from an upstream passageway segment to a downstream passageway segment and closes to prevent air from passing in an opposite direction through the check valve from the downstream segment to the upstream segment.