Continuous Queries (CQs) are designed to operate over infinite data streams; the paradigm gained prominence with the rise of Stream Processing (SPs). Central to CQs are window operators as they enforce bounded computation by partitioning streams into finite subsets. Although several window operators exist —e.g., slide-by-tuple, session-window, and frames—commercial systems largely adopt a few due to implementation complexity, theoretical opacity, and input-dependent non-determinism. This demonstration shows Play2Win, an interactive playground that empowers users to explore and compare various windowing strategies under a unified system semantics. Our platform offers three key contributions: (I) a real-time environment for experimenting with different window operators; (II) a graph-based representation of the window state that eases direct comparison; and (III) a compositional framework for rapid prototyping of novel windowing mechanisms. The demonstration explore multiple datasets across different scenarios, fostering a deeper understanding of window operators for querying streams.