Anxiety and difficulty in administering medication to nursery school children has been reported among nursery school teachers. This study aimed to elucidate these issues and explore the possibility of pharmacist support and collaboration. We conducted a postal survey in September 2019 among nursery schools in Tokyo that are categorized as government-authorized schools, certified childcare centers, and prefectural governor-certified schools. A total of 1,537 schools responded to the self-report questionnaires (response rate: 41.2%), and 1,533 responses were analyzed. Of these, 1,488 schools were asked if they would accept requests to administer medication to their school children, and 60.1% of the nursery schools responded that their staff (including teachers and nurses) found it difficult to administer medication. The issues identified included psychological burdens (such as nervousness and pressure about giving the correct medication), staff shortage, insufficient time with the children, and human factors (such as personal perceptions of medication). Additionally, excessive requests to administer medication, caregiver behavior such as low awareness of children’s health and appropriate medication, and poor medication adherence at home were identified as issues. It was suggested that pharmacists could help alleviate these problems through their daily work at the pharmacy. Approximately 49-62% of schools responded that they would request the collaboration of community pharmacists to conduct training sessions for nursery school staff, provide health support for caregivers, and provide general health and medication consultations. The collaboration between nursery schools and community pharmacists may gain importance in the future.