Matching BC550 and BC560

Depends on the grade (A-B-C), the design of the circuitry involved, and the vulnerability of the very circuit design to the variation within the grades.
This does not only counts for headphones, not specified various devices & other undefinded amblifiers...
 
Talk to the circuit designer. She will be able to tell you how closely they should be matched.

If that is inconvenient, hire an expert circuit designer who did not design the circuit. Show her the circuit schematic for the discrete headphone amblifier. Ask her (A) what her fee will be; and also (B) how closely those transistors should be matched.