This article examines the interconnections between mentoring and teacher collaboration in view of the intergenerational gap between experienced and novice educators in the post-Soviet Ukraine. The conceptual framework utilized a constructive postmodern perspective as an analytical lens and examined mentorship as a collaborative form of teacher development. Qualitative methods, such as document analysis, focus group interviews, and individual interviews, were used in this study. Collaboration among generations of teachers in schools was found to be susceptible to transformations at the macrolevel (societal) as well as the microlevel (school). The study suggests that the development of collaborative cultures in Ukrainian schools requires close attention to bridging the intergenerational gap between experienced and novice teachers by establishing lasting and deep working relationships through the systematic practice of mentorship.