Flashover on transmission line insulators is one of the major causes of line outages due to contamination from the environment or ageing. Power utility companies practicing predictive maintenance are currently exploring novel non-contact methods to monitor insulator surface discharge activities to prevent flashover. This paper presents an investigation on the UV pulse signals detected using UV pulse sensor due to the discharges on the insulator surfaces under varying contamination levels and insulator ages. Unaged and naturally aged insulators (0 to >20 years) were artificially contaminated (none, light to heavy contamination). The electrical stresses on the insulator surfaces were varied to generate varying discharge intensity levels on the surfaces of the insulator. The DC and harmonic components of UV pulse signals detected during surface discharges were recorded and analysed. Results show a positive correlation between the discharge intensity level of contaminated and aged transmission insulators with the DC and harmonic components of the UV pulse signals. Furthermore, the study revealed that under dry insulator surface conditions, insulator ageing has a more profound effect during discharges than contamination level. The findings from this study suggest that the use of UV pulse sensors to monitor UV pulse signals emitted during insulator surface discharges can be another novel non-contact method of monitoring transmission line insulator surface conditions.