This study aims to evaluate the potential role of pillboxes used for the preparation and delivery of individual daily medical treatments in the drug circuit of the Military Instruction Hospital (France) as reservoirs of bacterial contaminants. Samples were obtained from 32 pillboxes after decontamination (T1), after preparation in the pharmacy (T2), after use in two different medical units (T3), and again after usual mechanical washing (T4). Qualitative (identification and antibiotic susceptibility) and quantitative (contamination rate and number of colony forming units—CFUs) bacteriological tests were performed. Susceptible and resistant strains of environmental saprophytes were identified. The pillbox contamination rate was relatively low at T1 (13%). It was significantly increased at T2 (63%, p = 0.001 vs. T1), again at T3 (88%, p < 0.05 vs. T2, p < 0.001 vs. T1), and finally decreased dramatically at T4 (31%, p < 0.001 vs. T3, p > 0.05 vs. T1). The number of CFUs was significantly increased at T2 compared with that of T1 (36.7 ± 13.4 and 5.36 ± 3.64, respectively, p < 0.001) and again at T3 (84.4 ± 19.4, p < 0.001 vs. T1 and T2) and was significantly reduced at T4 (7.0 ± 2.0 vs. T3, p < 0.001) to a level that was not significantly different from that at T1. So, the use of pillboxes to deliver individual medications to patients in the hospital is a potential risk factor for bacterial cross-contamination.