Asphalt pavements subjected to vehicular loads deteriorate with time during their service life. This is reflected in the form of pavement distresses such as ruts in the wheel path, fatigue cracking, and potholes. Therefore, a study of the damage in asphalt mixes when subjected to stresses becomes essential. Damage assessment in a pavement structure can be done by both destructive and non-destructive methods. More recently, the use of non-destructive methods such as ultrasonic pulses have helped improve understanding of damage occurring within an asphalt sample. Damage in conventional asphalt mixes under mechanical stresses has been studied by researchers earlier using the above. Lately, crushed waste glass (CWG) is being explored as a possible alternative to the scarcely available natural aggregates used in asphalt mixes. This paper provides a comprehensive understanding of the evolution of fracture and damage occurring in CWG-based asphalt mixes with an increasing percentage of glass, when tested for their unconfined compressive strength (UCS). This has been achieved with real-time active monitoring of ultrasonic pulses during the loading process controlled with LabVIEW. Results indicate interesting differences in wave velocity, amplitude, energy, and ultimately extent of damage in the mix designs with and without glass.