Road cycling, both individually and in groups, is common in Spain, where most two-lane rural roads have no cycle lanes. Due to this, and the difference in speed between drivers and cyclists, the overtaking manoeuvre is one of the most dangerous interactions. This study analyses how road geometry influences the overtaking manoeuvre performance. Field data of 1355 overtaking manoeuvres were collected using instrumented bicycles, riding along different rural road segments, and considering individual, medium and large groups of cyclists. The safety variables that characterise the overtaking manoeuvre are overtaking vehicle speed and lateral clearance. These variables have been correlated to geometric characteristics of the road, such as the type of centre line, the horizontal alignment, the speed limit, and the road cross section. Regression models have been fitted considering each cyclist group size and configuration. For individuals and medium groups, wider roads generate higher lateral clearances and lower overtaking speeds, while for large groups only the solid centre line was significant, generating lower clearances and higher speeds. Results suggest that other factors need to be considered, especially for large groups. Results offer a deeper understanding of the phenomenon by providing key points for improving road geometry design, such as widening the shoulders.