In the absence of cross-winds, a cyclist can expend up to 90% of their energy to overcome drag and can save up to 30% of that energy if riding behind another cyclist. The aerodynamic forces acting on cyclists in the presence of cross wind have not been studied in much detail. The effect of the offset distances between cyclists on the aerodynamic forces has been investigated in the literature for configurations of two cyclists. In the present study, 1:11 scale models of two different cyclists were rapid-prototyped and tested in a wind tunnel. The effect of the size of the cyclist was studied by placing the larger cyclist model behind the smaller one; the smaller behind the larger one; and the larger model behind an identical (larger model) copy. The effect of position within the group was studied by measuring the forces on each of the four cyclists placed in a favorable formation. The results suggest that the size of the cyclist matters, particularly when the leading cyclist is smaller than the drafting cyclist, and the effect is more prominent for the side forces. The results also show that in a formation of four cyclists, the leading cyclist experiences minor drag reduction compared to riding alone. The second and third cyclists experience the largest force reductions within the group, and the fourth cyclist experiences force reduction, which is not as significant. The results appear to be dependent on the Reynolds number, but may still be valuable for racing strategies and recreational cycling.