This work evaluates the effect of high temperatures and cooling methods on the drillability of Prada limestone. Samples from boreholes drilled during the design stage of the Tres Ponts Tunnel in the Catalan south Pyrenean zone (Spain) were subjected to temperatures of 105, 200, 300, 400, and 600 °C, and then cooled at a slow rate or by quenching. Sievers’ J-value (SJ) and brittleness (S20) were determined on thermally treated samples, and the drilling rate index (DRI) was calculated for each temperature. The results show that thermal treatment implied a sustained increase in the drillability of the rock of up to 40% at 600 °C and a change in the drillability category (from medium to high). At 600 °C, SJ and S20 tripled and doubled, respectively, the initial values obtained for the intact rock. The results were inconclusive about the influence of the cooling method on the drilling performance of Prada limestone for the tested range of temperatures. The substantial improvement observed in the drillability of Prada limestone when heated, measured in terms of DRI, could help in the development of novel thermally-assisted mechanical excavation methods. Additionally, strong correlations between drillability variables (i.e., SJ and S20) and physical and mechanical variables of Prada limestone (i.e., P- and S-wave velocities, uniaxial compression strength, elastic modulus, and Poisson’s ratio) are proposed. Correlations will help make preliminary predictions of drillability based on properties such as uniaxial compression strength and ultrasound wave velocities.