Abstract-This work presents an evaluation of the measurement challenges in clinical testing of our microwave breast cancer screening system. The time-domain radar system contains a multistatic 16-antenna hemi-spherical array operating in the 2-4 GHz frequency range. We investigate, for the first time with such a system in clinical trials, the repeatability of measurements and its effect on image reconstruction. We record vertical and horizontal measurement uncertainties under different scenarios and verify using previously introduced compensation methods that they can be successfully reduced to an acceptable level from the standpoint of image reconstruction. We also examine how placement of an immersion medium can affect collected breast scan data. Finally, we probe the repeatability and consistency of measurements with patients. With the goal of confirming the feasibility of frequent breast health monitoring, with our system, we obtain a total of 342 breast scans collected over 57 patient visits to determine how much scan data varies when there are no changes in between scans, and how much it varies when the patient is repositioned in the system. We confirm that, by taking care in patient positioning in the system and with respect to the immersion medium, the measurement repeatability is high.