The continuously increasing energy density of electric motors to match the performance of electric vehicles with internal-combustion-engine vehicles demands an advanced cooling strategy. Direct dripping/spray cooling is one of such potential cooling strategies to replace the conventional cooling method for achieving the desired thermal management of next-generation electric motors. In the present work, the heat transfer characteristics of an electric motor with oil-dripping cooling were experimentally investigated considering overload operating conditions. An experimental set-up comprising a 15 kW electric motor and an oil-dripping cooling system was developed. The experimental data were used to evaluate the maximum temperature, heat transfer coefficient and power consumption under the influence of a dripping hole diameter (2 mm, 3 mm, 4 mm), oil flow rate (8 LPM, 12 LPM, 16 LPM) and overload operating power (8.28 kW, 12.05 kW, 14.21 kW). The symmetrical oil distribution over the electric motor and the superior heat transfer from the electric motor to the oil was achieved when the oil-dripping cooling system was designed with the combination of a 4 mm dripping hole diameter and a 12 LPM oil flow rate. The combination of the 4 mm dripping hole diameter and 12 LPM oil flow rate showed the lowest maximum temperatures of 31.9 °C and 46.3 °C for electric motor under overload operating powers of 8.28 kW and 14.21 kW, respectively. In addition, the highest heat transfer coefficient of 7528.61 W/m2-K and lowest power consumption of 18.07 W were achieved for the oil-dripping cooling system with the combination of a 4 mm dripping hole diameter and 12 LPM oil flow rate. The best combination of the operating parameters is proposed for developing the oil-dripping cooling system that enables superior heat transfer characteristics and, thus, an enhanced thermal management of electric motors under overload conditions.