Generally, the insulation degradation and contacts failure happened inside the On Load Tap Changer (OLTC). Besides, the OLTC performance can be dropped due to contact wear. Hence., the worn contact creates hotspots inside OLTC tank and affects the insulating oil. Due to this phenomenon, the insulating oil will degrade faster. Consequently, the whole unit of the transformer will be affected as well. Therefore, it is important to find new ways to detect the contacts wear inside the OLTC as it impacts the insulation oil and the age of the transformer. Thus, this paper demonstrates the application of Duval Triangle method during the diagnosis of OLTC to provide any significant indication related to the breakdown of OLTC. Besides, this paper introduced the advanced technique, Dynamic Winding Resistance Measurement (DWRM) to figure out the types and locations of faults occurred inside the OLTC. Finally, visual inspections will be carried out to validate the both results obtained from DGA and DWRM respectively. The analysis in this paper revealed that the findings from Duval Triangle method were similar to the outcomes carried out by DWRM.