An exemplary method includes generating a digit map in response to user input received by way of a graphical user interface, the digit map defining a digit sequence and a plurality of dual-tone multi-frequency (“DTMF”) properties associated with each digit included in the digit sequence, generating DTMF tones representing the digit sequence in accordance with the DTMF properties, transmitting the DTMF tones to a gateway device communicatively coupled to the testing subsystem, the gateway device configured to translate the DTMF tones into a packet-based representation of the digit sequence and the DTMF properties, receiving the packet-based representation of the digit sequence and the DTMF properties from the gateway device, and determining whether the digit sequence and the DTMF properties included in the packet-based representation substantially match the digit sequence and the DTMF properties defined by the digit map. Corresponding methods and systems are also disclosed.