With continuous improvements, structural steels are available in even higher strength grades above 1000 MPa yield strength. As the great majority of these steels are used in welded structures, their weldability needs to be taken into account. Several factors can cause difficulties during welding of these steels, but in this paper the softening behavior and the toughness characteristics of the heat-affected zone (HAZ) are examined. As the critical parts of the HAZ in a real welded joint are relatively small, their investigating ability is limited. However, the physical simulation provides a way of evaluating specimens made from a given material to produce the specified HAZ areas in a suitable size range for subsequent testing. In this research work, three different strength categories of high-strength structural steels (with yield strength of 960 MPa, 1100 MPa, and 1300 MPa) are investigated by physical simulation. In the case of different technological variants of gas metal arc welding (GMAW) process, the effect of the cooling time t8/5 is investigated in different HAZ subzones considered to be critical. The thermal cycles were determined according to the Rykalin 3D model. The investigated cooling times were t8/5 = 5 s, 15 s, and 30 s. The properties of the selected coarse-grained, intercritical and intercritically reheated coarse-grained zones are analyzed by laser scanning microscope, scanning electron microscope, hardness test, and instrumented Charpy V-notch impact toughness test. Furthermore, additional investigation like JMatPro calculations, electron backscatter diffraction measurements, and prior austenite grain size calculation were carried out. As a result of the tests, the investigated heat-affected subzones indicated higher sensitivity to the welding heat input compared to conventional structural steels. Overall, the results of the tests show that the application of shorter t8/5 cooling time can be beneficial for the investigated high-strength steel grades, since significant toughness reduction and the risk of softening occur in the whole cooling time range.