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It is now well-accepted that the cerebrovascular system does not merely provide inert pipes for blood delivery to the brain. Cerebral endothelial cells may compose an embedded bunker of trophic factors that contribute to brain homeostasis and function. Recent findings suggest that soluble factors from cerebral endothelial cells nourish neighboring cells, such as neurons and astrocytes. Although data are strongest in supporting mechanisms of endothelium–neuron and/or endothelium–astrocyte trophic coupling, it is likely that similar interactions also exist between cerebral endothelial cells and oligodendrocyte lineage cells. In this chapter, we summarize current advances in the field of endothelium–oligodendrocyte trophic coupling. These endothelium–oligodendrocyte interactions comprise the oligovascular niche and sustain ongoing angiogenesis/oligodendrogenesis. Importantly, these cell–cell interactions are not static—the trophic coupling is disturbed during the acute phase after brain injury, with the potential to recover in the chronic phase to promote brain remodeling and repairing. Oligodendrocyte lineage cells play critical roles in white matter function. Therefore, a deeper understanding of the mechanisms of endothelium–oligodendrocyte trophic coupling may lead to new therapeutic approaches for diseases related to white matter pathology, such as stroke or vascular dementia.