The flow around a circular cylinder at Reynolds number of 1.4 × 105 is examined with Reynolds-Averaged Navier–Stokes equations (RANS) and Scale-Resolving Simulation (SRS) methods. Such problem is in the upper limit of the flow regime where turbulent transition occurs in the free shear-layers and so the flow dynamics is dominated by the spatial development of vortex-shedding structure, and in particular by the Kelvin–Helmholtz rollers and turbulence onset. The objectives of this investigation are threefold: (i) determine the aptitude of distinct RANS and SRS models to simulate the correct flow regime; (ii) compare the predictions of selected methods with available experimental measurements; and (iii) examine key modelling and flow features that contribute to the observed results. The evaluated models range from RANS supplemented with linear, transition, and non-linear turbulent viscosity closures, to hybrid and bridging SRS methods. Bridging computations are conducted at various constant degrees of physical resolution (range of resolved scales). The results illustrate the complexity of predicting the present flow problem. It is shown that RANS and SRS formulations modelling turbulence in boundary-layers with the selected linear turbulent viscosity closures lead to a premature onset of turbulence which alters the flow regime of the simulations. Although the transition and non-linear RANS closures can predict the correct flow regime, the outcome of this study indicates that solely the bridging model at constant physical resolution is able to achieve an accurate and physics-based prediction of the flow dynamics. Nonetheless, the necessary degree of physical resolution makes the numerical requisites of such computations demanding.