The difficulty and anxiety of nursery staff in administering medication to children at nursery schools has been reported, and its reduction is desired. However, the attitudes of mothers in requesting medication and the factors related to a high frequency of requests are not clear. We conducted an online survey of 600 mothers from April to May 2019 regarding the administration of medication at nursery school, and 301 mothers who had previously made such requests were analyzed. The results showed that 100.0% and 76.4% of the mothers felt gratitude and were apologetic for requesting medicine administration, respectively. In total, 47.5% of mothers expected pharmacists to support nursery staff in administering medication. Mothers’ attitude of “I think the nursery staff should administer medication to my child more often” was significantly positively associated with a high frequency of the request in adjusted Model (adjusted odds ratio [AOR] 2.75, 95% confidence interval [CI] 1.36-5.55, p = 0.005), while “I think the parents should manage so that the children do not have to take medicine in the nursery school so often.” showed a negative association (AOR 0.33, 95% CI 0.17-0.66, p = 0.002). Factors related to the involvement of community pharmacists were not significant. It is suggested that a change in mothers’ attitudes could decrease the frequency of requests and consequently reduce the burden on nursery staff. Community pharmacists may support nursery staff to contribute to changing mothers’ attitudes through medication consultations at the pharmacy.