This study presents the investigations on Partial Discharge (PD) behaviour of irregular-shaped copper particle in oil with pressboard barrier placed in two positions under uniform field with different moisture contents. Frequency Domain Spectroscopy (FDS) was used to estimate percentage moisture in pressboard. Recovery Voltage Measurement was used to confirm obtained FDS results. PD characteristics like magnitude, number, discharge power, rise time and duration time of PD pulse were analysed. Electric field due to particle in oil with moisture content pressboard barrier was studied by simulations. Phase Resolved PD (PRPD) pattern for different moisture pressboard observed to have similar patterns with variation in PD inception voltage (PDIV), magnitude and number of discharges. It was observed that PD characteristics as a function of voltage, increases nearly quadratic rate with respect to percentage moisture in pressboard. Simulation results complimented experimentally measured PDIV values for particle in oil with moisture in pressboard. Filtering and conditioning of oil is mandatory practice in a new transformer before going to any high voltage (HV) applications. PRPD pattern and PD characteristics data obtained in this study has great practical significance to assess the condition of transformer insulation systems before proceeding for HV application to avoid any potential failure.