We present a behavioural typing system for a higher-order timed calculus using session types to model timed protocols. Behavioural typing ensures that processes in the calculus perform actions in the time-windows prescribed by their protocols. We introduce duality and subtyping for timed asynchronous session types. Our notion of duality allows typing a larger class of processes with respect to previous proposals. Subtyping is critical for the precision of our typing system, especially in the presence of session delegation. The composition of dual (timed asynchronous) types enjoys progress when using an urgent receive semantics, in which receive actions are executed as soon as the expected message is available. Our calculus increases the modelling power of extant calculi on timed sessions, adding a blocking receive primitive with timeout and a primitive that consumes an arbitrary amount of time in a given range.