The study aims to address the question of how intergenerational learning (IGL) among teachers takes place in various educational leadership contexts. We present an answer based on three case studies of schools with different approaches to educational leadership, each employing various support measures. We describe IGL within these three settings. We show how educational leadership influences the contents, the depth, and the density of IGL interactions. We conclude that more widespread IGL interactions might be secured by the general support of functional relationships among teachers. This kind of support is not able, in and of itself, to promote deeper learning. Deep and teachers in charge, b) the development of skills to give and receive support and feedback, and c) the accepted belief that IGL can be inspirational and beneficial for professional learning for each teacher no matter the generation.