In this work, we revisit the non-minimally coupled Higgs Inflation scenario and investigate its observational viability in light of the current Cosmic Microwave Background, Baryon Acoustic Oscillation and type Ia Supernovae data. We explore the effects of the Coleman-Weinberg approximation to the Higgs potential in the primordial universe, connecting the predictions for the Lagrangian parameters at inflationary scales to the electroweak observables through Renormalization Group methods at two-loop order. As the main result, we find that observations on the electroweak scale are in disagreement with the constraints obtained from the cosmological data sets used in the analysis. Specifically, an $approx 8sigma$-discrepancy between the inflationary parameters and the electroweak value of the top quark mass is found, which suggests that a significant deviation from the scenario analysed is required by the cosmological data.