A driving evaluation system includes: a driving information acquisition unit that acquires driving information related to driving of a driver of a vehicle; a driving evaluation calculation unit that calculates a driving evaluation result obtained by evaluating the driving of the driver based on the driving information acquired by the driving information acquisition unit; a timing determination unit that determines a timing at which the driving evaluation result is output for each output destination; and an evaluation result output unit that outputs the driving evaluation result at the timing determined by the timing determination unit.