The interaction between guest chromophores or lumiphores with host chiral cavity and their induced chirality is an important topic in supramolecular chemistry. Kodaka and Harata proposed a rule to explain the induced circular dichroism of the guest chromophores by host cyclodextrins. However, it remains unknown how a circularly polarized luminescence (CPL) signal will change when the lumiphores interacted with cyclodextrins in different modes. Here, we designed an achiral pyrene-adamantane conjugated guest molecule, N-(pyren-1-yl)adamantane-1-carboxamide (ACNP), and investigated its interactions with α/β/γ-cyclodextrins (CDs) and its induced CPL. Depending on the size match of the pyrene, adamantine with different cyclodextrins, distinct performance was observed. While α-CD could not induce a CPL signal of ACNP, β-CD could induce CPL in two modes, through adamantyl or direct pyrenyl induction, which could produce a CPL signal with opposite signs. γ-CD could always induce a negative CPL signal. Therefore, a rule of induced CPL of lumiphores by cyclodextrins can be proposed.