Abstract: The measured branching fractions of B-mesons into leptonic final states derived by the LHCb, Belle and BaBar collaborations hint towards the breakdown of lepton flavour universality. In this work we take at face value the so-called R-D(()*()) observables that are defined as the ratios of neutral B-meson charged-current decays into a D-(*())-meson, a charged lepton and a neutrino final state in the tau and light lepton channels. A well-studied and simple solution to this charged current anomaly is to introduce a scalar leptoquark S-1 that couples to the second and third generation of fermions. We investigate how S-1 can also serve as a mediator between the Standard Model and a dark sector. We study this scenario in detail and estimate the constraints arising from collider searches for leptoquarks, collider searches for missing energy signals, direct detection experiments and the dark matter relic abundance. We stress that the production of a pair of leptoquarks that decays into different final states (i.e. the commonly called “mixed” channels) provides critical information for identifying the underlying dynamics, and we exemplify this by studying the t tau b nu and the resonant S-1 plus missing energy channels. We find that direct detection data provides non-negligible constraints on the leptoquark coupling to the dark sector, which in turn affects the relic abundance. We also show that the correct relic abundance can not only arise via standard freeze-out, but also through conversion-driven freeze-out. We illustrate the rich phenomenology of the model with a few selected benchmark points, providing a broad stroke of the interesting connection between lepton flavour universality violation and dark matter.