Epichloë species with their asexual states are specialized fungi associated with cool-season grasses. they grow endophytically in tissues of aerial parts of host plants to form systemic and mostly asymptomatic associations. Their life cycles may involve vertical transmission through host seeds and/or horizontal transmission from one plant to other plants of the same species through fungal propagules. Vertical transmission has been well studied, but comparatively little research has been done on horizontal dissemination. The goal of this review is to provide new insights on modes of dissemination of systemic grass endophytes. The review addresses recent progress in research on (i) the process of growth of Epichloë endophytes in the host plant tissues, (ii) the types and development of reproductive structures of the endophyte, (iii) the role of the reproductive structures in endophyte dissemination and host plant infection processes and (iv) some ecological and evolutionary implications of their modes of dissemination. Research in the Epichloë grass endophytes has accelerated in the past 25 y and has demonstrated the enormous complexity in endophyte-grass symbioses. There still remain large gaps in our understanding of the role and functions of these fungi in agricultural systems and understanding the functions, ecology and evolution of these endophytes in natural grass populations.