In North America, highway agencies have started using Superpave as it incorporates a performance-based asphalt binder specification and a mix design analysis system. However, in a pavement management system (PMS), the performance of the pavement structure significantly influences management decisions. In this regard, accurate prediction and evaluation of performance is a very important aspect. With this in mind, this study investigates the performance of Superpave through the mechanistic–empirical (M-E) approach, field-evaluated performance, and laboratory performance tests. It considers 15 sections of highways from Ontario. The investigation found that the international roughness index (IRI) and permanent deformation are overpredicted in the M-E approach compared with field observations. Additionally, to better understand the performance, the dynamic modulus of asphalt mixtures and binder rheological testing are also performed. The master curve developed for the surface mixtures suggests a lower level of fatigue resistance that justifies the bottom-up fatigue failure in the field-observed scenarios.