This paper shares the experiences from the application of AR using the pro-cam robot assistant to managing children's play from three user perspectives, namely, the operator (teacher), the actors (children), and the audience (mainly children). First a preliminary expert survey was conducted to assess the expected benefits and any particular provisions needed both educationally and technically. Based on the expert survey, the original implementation was slightly modified, particularly for the robot control interface design for the teachers (e.g. to support easier multi-tasking). Finally, a formative evaluation and analysis was conducted to assess the educational effects to the children (both actors and audiences) and their attitudes when a pro-cam robot was used to run an AR based play, as compared to when a conventional approach was used. The study has found that robot-assisted AR based play showed improved learning effects, compared to the conventional play, in language and creativity and this is attributed to the operational flexibility, novelty, robotic mediation and capturing the attention of the children. The result was also made possible in part by designing an effective interface for the teachers to control the robots and manage the simultaneously occurring tasks.