Overhead conductors for transmission lines are subjected to cyclic loading due to Aeolian vibration which can lead to the failure of their wires. One of the most critical transmission power line points where fatigue failure occurs is the vicinity of the assembly consisting of the conductor and the suspension clamp. This work evaluates the fatigue life of assemblies made by two types of conductors, i.e., All Aluminium Alloy Conductor (AAAC) 1120 and 6201. Furthermore, metallic and elastomeric clamps are examined. Based on the generated S-N and ${\boldsymbol{f}}{{\boldsymbol{y}}_{{\boldsymbol{max}}}}$-N graphs, it was proved that the assembly AAAC 1120 with elastomeric clamp presented a better fatigue performance than the other three assemblies. Additionally, the change in fatigue life was investigated, failure and contact marks analyses were also performed on all samples after the fatigue test with respect to the conductor layer where the failure occurred as well as the types of break and the position of wires’ break (whether radial and longitudinal position).