Car manufacturers expect driving simulators to be reliable research and development tools. Questions arise, however, as to whether drivers’ behavior on simulators exactly matches that observed when they are driving real cars. Drivers’ performances and their subjective feelings about their driving were compared between two groups during a 40-min driving test on the same circuit in a real car (n = 20) and a high-fidelity dynamic simulator (n = 27). Their speed and its variability, the braking force and the engine revolutions per minute (rpm) were recorded five times on a straight line and three times on a curve. The differences observed in these measurements between circuit driving (CD) and simulator driving (SD) from the 6th to 40th minute showed no significant changes during the drive. The drivers also completed the NASA Raw Task Load Index (NASA RTLX) questionnaire and the Simulator Sickness Questionnaire (SSQ) and estimated the ease and standard of their own driving performances. These subjective feelings differed significantly between the two groups throughout the experiment. The SD group’s scores on the NASA RTLX and SSQ questionnaires increased with time and the CD group’s perceived driving quality and ease increased with time, reaching non-significantly different levels from their usual car driving standards by the end of the drive. These findings show the existence of a fairly good match between real-life and simulated driving, which stabilized six minutes after the start of the test, regardless of whether the road was straight or curved. These objective findings and subjective assessments suggest possible ways of improving the match between drivers’ performances on simulators and their real-life driving behavior.