In order to evaluate the insulation deterioration in the stator windings of five gas turbine generators(137 MVA, 13.8 kV) which has been operated for more than 13 years, diagnostic test and AC dielectric breakdown test were performed at phases A, B and C. These tests included measurements of AC current, dissipation factor, partial discharge (PD) magnitude and capacitance. ${Delta}I$ and ${Delta}tan{delta}$ in all three phases (A, B and C) of No. 1 generator stator windings showed that they were in good condition but PD magnitude indicated marginally serviceable and bad level to the insulation condition. Overall analysis of the results suggested that the generator stator windings were indicated serious insulation deterioration and patterns of the PD in all three phases were analyzed to be internal, slot and spark discharges. After the diagnostic test, an AC overvoltage test was performed by gradually increasing the voltage applied to the generator stator windings until electrical insulation failure occurred, in order to determine the breakdown voltage. The breakdown voltage at phases A, B and C of No. 1 generator stator windings failed at 28.0 kV, 17.9 kV, and 21.3 kV, respectively. The breakdown voltage was lower than that expected for good-quality windings (28.6 kV) in a 13.8kV class generator. In the AC dielectric breakdown and diagnostic tests, there was a strong correlation between the breakdown voltage and the voltage at which charging current increases abruptly ($P_{i1}$, $P_{i2}$).