The involvement of cyclists in road crashes has not been decreasing with the same magnitude as the involvement of other road users. In particular, the interactions between cyclists and motorized traffic can lead to high-severity crashes. To improve the safety of these interactions, a thorough understanding of road user behaviour is first needed. In this study, we focused on drivers overtaking cyclists on rural roads. The two main objectives of this study were to develop models that predicted: (a) drivers’ decisions to perform either a flying or an accelerative overtaking manoeuvre in the presence of oncoming traffic, and (b) the lateral comfort distance that drivers maintain from cyclists during the overtaking. A driving simulator study was designed to assess driver decision-making during the overtaking. The 37 drivers who participated in the study each performed seven overtaking manoeuvres with oncoming traffic. Out of the 259 overtaking manoeuvres, 168 were flying and 91 were accelerative. Binary logistic-regression models with mixed effects predicted the type of overtaking strategy (flying or accelerative). Driving speeds were found to significantly affect the strategy. The overall performance of the models predicting the strategy was 85–90%. Models were also developed for predicting the lateral comfort distance. The results show that the lateral comfort distance is mostly affected by the longitudinal distance between the subject vehicle and the oncoming vehicle, the longitudinal distance between the subject vehicle and the cyclist, and the presence of an oncoming vehicle—as well as by the drivers’ characteristics (sensation seeking in flying overtaking manoeuvres and ordinary violations in accelerative manoeuvres). The root mean square error, which was used to assess the performance of the models, ranged from 0.56 to 0.62. In conclusion, the models predicting the overtaking strategy performed reasonably well, while the models predicting lateral distance did not provide accurate predictions. The models predicting overtaking strategy may support (1) the development and evaluation of active safety systems, (2) the design of automated driving, and (3) policy making.@en