A liquid medicine filling device is provided with a container mounting unit, a liquid delivery flow path, a ventilation flow path, a syringe, a connection flow path, a first flow path switching unit, and a second flow path switching unit. The first flow path switching unit may switch between a flow path for filling through which the syringe is communicated with a liquid medicine container via the ventilation flow path and a flow path for air removal through which the syringe is communicated with the connection flow path via the ventilation flow path. The second flow path switching unit may switch between a flow path for filling through which the liquid medicine container is communicated with the liquid medicine storage unit via the liquid delivery flow path and a flow path for air removal through which the liquid medicine storage unit is communicated with the connection flow path via the liquid delivery flow path.