Nanodevices based on monolayer black phosphorus or phosphorene are promising for future electron devices in high density integrated circuits. We investigate bandstructure and size-scaling effects in the electronic and transport properties of phosphorene nanoribbons (PNRs) and the performance of ultra-scaled PNR field-effect transistors (FETs) using advanced theoretical and computational approaches. Material and device properties are obtained by non-equilibrium Green’s function (NEGF) formalism combined with a novel tight-binding (TB) model fitted on ab initio density-functional theory (DFT) calculations. We report significant changes in the dispersion, number, and configuration of electronic subbands, density of states, and transmission of PNRs with nanoribbon width (W) downscaling. In addition, the performance of PNR FETs with 15 nm-long channels are self-consistently assessed by exploring the behavior of charge density, quantum capacitance, and average charge velocity in the channel. The dominant consequence of W downscaling is the decrease of charge velocity, which in turn deteriorates the ON-state current in PNR FETs with narrower nanoribbon channels. Nevertheless, we find optimum nanodevices with W > 1.4 nm that meet the requirements set by the semiconductor industry for the “3 nm” technology generation, which illustrates the importance of properly accounting bandstructure effects that occur in sub-5 nm-wide PNRs.