A stethoscope disinfection monitoring and reporting system structured and configured to track, monitor and report the cleaning, disinfecting, and/or sterilizing of the head portion of a stethoscope is presented. The system comprises a stethoscope cleaning assembly cooperatively structured and configured to clean the head portion of the stethoscope, for instance, via the application of a cleaning fluid or solution thereto. The system further comprises a monitoring device and a cooperatively structured and disposed reader assembly. The monitoring device may be unique to, or otherwise serve to identify, the stethoscope. The reader assembly is structured and disposed to detect, identify, and record data pertaining to the monitoring device and/or stethoscope upon cleaning the head portion, or otherwise upon disposition of the head portion into a cleaning relation with the stethoscope cleaning assembly.