Brain asymmetry is connected with motor performance, suggesting that hemiparetic patients have different gait patterns depending on the side of the lesion. This retrospective cohort study aims to further investigate the difference between right and left hemiplegia in order to assess whether the injured side can influence the patient’s clinical characteristics concerning gait, thus providing insights for new personalized rehabilitation strategies. The data from 33 stroke patients (17 with left and 16 with right hemiplegia) were retrospectively compared with each other and with a control group composed of 20 unaffected age-matched individuals. The 3D gait analysis was used to assess kinematic data and spatio-temporal parameters. Compared to left hemiplegic patients, right hemiplegic patients showed worse spatio-temporal parameters (p < 0.05) and better kinematic parameters (p < 0.05). Both pathological groups were characterized by abnormal gait parameters in comparison with the control group (p < 0.05). These findings show an association between the side of the lesion—right or left—and the different stroke patients’ gait patterns: left hemiplegic patients show better spatio-temporal parameters, whereas right hemiplegic patients show better segmentary motor performances. Therefore, further studies may develop and assess new personalized rehabilitation strategies considering the injured hemisphere and brain asymmetry.