Nowadays, the use of wearable inertial-based systems together with machine learning methods opens new pathways to assess athletes’ performance. In this paper, we developed a neural network-based approach for the estimation of the Ground Reaction Forces (GRFs) and the three-dimensional knee joint moments during the first landing phase of the Vertical Drop Jump. Data were simultaneously recorded from three commercial inertial units and an optoelectronic system during the execution of 112 jumps performed by 11 healthy participants. Data were processed and sorted to obtain a time-matched dataset, and a non-linear autoregressive with external input neural network was implemented in Matlab. The network was trained through a train-test split technique, and performance was evaluated in terms of Root Mean Square Error (RMSE). The network was able to estimate the time course of GRFs and joint moments with a mean RMSE of 0.02 N/kg and 0.04 N·m/kg, respectively. Despite the comparatively restricted data set and slight boundary errors, the results supported the use of the developed method to estimate joint kinetics, opening a new perspective for the development of an in-field analysis method.