A good number of studies were performed on the fatigue characterization of natural rubbers (NR) filled with Caron Nanotubes (CNTs). However, less attempts were given to: (i) understand how dispersion techniques employed in compounding CNTs/NR can affect the dynamic properties of NR as each dispersion approach can lead to different microstructural characteristics in terms of state of CNT dispersion and pores, (ii) have deep grasping of damage evolution in CNTs/NR nanocomposites at macro and micro scales. Therefore, this study was aimed to investigate the fatigue life of CNTs filled natural rubbers prepared by two different compounding techniques including wet and dry methods. This was done to correlate the presence of defects to fatigue performance and to find out the optimum dispersion approach for CNTs/NR compounding. The wet approach possessed higher number of large defects compared to the dry approach whereas the latter method manifested better CNT dispersion. The presence of a higher number of large defects including voids were accounted for a significant reduction of the fatigue life in the wet batch with respect to dry samples. Formation of multiple tiny cracks and their further developments via crack-shielding and crack-coalescence were considered for damage evolution at the macro-scale while the presence of wrenching, resulting from Strain Induced Crystallization (SIC), and river-like patterns on fracture surfaces were notable at the micro-scale. It was concluded that the dry approach could be a better compounding technique for the CNT dispersion considering its high quasi-static and fatigue properties, less environmental concerns thanks to no usage of solvent and cost effectiveness.