This paper focuses on assessing the failure of one of the transmission towers that collapsed in Winnipeg, Canada, as a result of a microburst event. The study is conducted using a fluid-structure numerical model that was developed in-house. A major challenge in microburst-related problems is that the forces acting on a structure vary with the microburst parameters including the descending jet velocity, the diameter of the event and the relative location between the structure and the jet. The numerical model, which combines wind field data for microbursts together with a non-linear finite element formulation, is capable of predicting the progressive failure of a tower that initiates after one of its member reaches its capacity. The model is employed first to determine the microburst parameters that are likely to initiate failure of a number of critical members of the tower. Progressive failure analysis of the tower is then conducted by applying the loads associated with those critical configurations. The analysis predicts a collapse of the conductors cross-arm under a microburst reference velocity that is almost equal to the corresponding value for normal wind load that was used in the design of the structure. A similarity between the predicted modes of failure and the post event field observations was shown.