We develop numerical tools for diagrammatic Monte Carlo simulations of non-Abelian lattice field theories in the t'Hooft large-N limit based on the weak-coupling expansion. First, we note that the path integral measure of such theories contributes a bare mass term in the effective action which is proportional to the bare coupling constant. This mass term renders the perturbative expansion infrared-finite and allows us to study it directly in the large-N and infinite-volume limits using the diagrammatic Monte Carlo approach. On the exactly solvable example of a large-N O(N) sigma model in D = 2 dimensions we show that this infrared-finite weak-coupling expansion contains, in addition to powers of bare coupling, also powers of its logarithm, reminiscent of resummed perturbation theory in thermal field theory and resurgent trans-series without exponential terms. We numerically demonstrate the convergence of these double series to the manifestly nonperturbative dynamical mass gap. We then develop a diagrammatic Monte Carlo algorithm for sampling planar diagrams in the large-N matrix field theory, and apply it to study this infrared-finite weak-coupling expansion for large-N U(N) x U(N) nonlinear sigma model (principal chiral model) in D = 2. We sample up to 12 leading orders of the weak-coupling expansion, which is the practical limit set by the increasingly strong sign problem at high orders. Comparing diagrammatic Monte Carlo with conventional Monte Carlo simulations extrapolated to infinite N, we find a good agreement for the energy density as well as for the critical temperature of the "deconfinement" transition. Finally, we comment on the applicability of our approach to planar QCD at zero and finite density.