Corona activity on the surface of silicone rubber has high impact on variation in hydrophobicity of the material, and on corona inception voltage (CIV) of water droplet sitting on the corona degraded surface. The CIV is high under negative DC as compared to positive DC/AC voltages. Increase in conductivity of water droplet reduces CIV. Surface charge accumulation studies indicate that the charge retention capability of the insulating material gets reduced drastically with silicone rubber damaged due to corona causing degradation of surface. Irrespective of the number of cycles of corona discharge activities carried out, the time constant of charge decay, after the removal of charge injection, remains the same. The water droplet initiated discharges under AC and DC voltages radiate UHF signal in the bandwidth 0.3-1.2 GHz. With single droplet sitting on top of the corona damaged silicone rubber, the amount of charge retained by the water droplet is low when the droplet is placed and charged immediately after corona discharge activity to surface of the insulating material. When the water droplet is placed after a certain time period, the charge accumulation characteristics of silicone rubber are regained. Leakage current measured during water droplet discharge studies through recurrent plot (RP) analysis reveals that, under AC voltage, it is possible to classify corona inception, arcing and bridging of water droplet between high voltage and ground electrode. The RP obtained for the current signals generated due to water droplet discharges under positive and negative DC voltages are different. The amount of damage caused to silicone rubber due to water droplet is high under negative DC voltage as compared to positive/AC voltages. While correlating the level of damage to the insulating material due to water droplet and the RQA parameters of RP, it is observed that higher the recurrence rate along with high determinism can cause severe damage to the insulating material. Structural analysis using ATR-FTIR and pyrolysis-GC/MS studies reveal significant functional group variation on surface of silicone rubber, especially when the number of cycles of corona ageing is more. © 2017 IEEE.