The present laboratory study investigates the behavior of a self-propagating barotropic cyclonic vortex colliding perpendicularly with aligned circular cylinders and determines the condition for a vortex to bifurcate and split into multiple vortices and/or to generate dipoles downstream of the cylinders. During the experiments, four parameters were varied: G, the gap width between the cylinders; d, the diameter of the incident vortex; Y dis , a parameter expressing the initial vortex positions; and D isl , the total length of the “middle” island. It has been observed that as long as 0.1 < G/d ? 0.4, the vortex fluid was funneled between two cylinders at one of the gaps and a dipole generally formed, much like water ejected from a circular nozzle generates a dipole ring. After the dipole formed, the cyclonic part of the dipole became dominant and self propagated away from the cylinders. Furthermore, in some experiments having 0.2 < D isl /d ? 0.5, after a weak dipole formed, the remnant of the original vortex moved zonally “south.” When the remnant of the vortex came in contact with a new cylinder, fluid peeled off the outer edge of the vortex and a so-called “streamer” went around the cylinder in a counterclockwise direction. Under the right conditions, this fluid formed a new cyclonic vortex in the wake of the cylinder, causing bifurcation of the original vortex into two vortices, as observed in previous studies. In general, independently of the configurations and Y dis , the number of cyclonic vortices downstream of the cylinders was one, either originating from the dipole or generated by the bifurcation of the original vortex. The vortex center position, radius, and circulation, before and after the interaction, were computed from its velocity field. It was found that for 0.1 < G/d ? 0.4, intense vortices experienced greater amplitude loss than weak vortices. The formation of both a dominant cyclone and an anticyclone (i.e., a dipole) downstream of the aligned cylinders, representing an island chain, is in agreement with recent oceanic observations of North Brazil Current (NBC) rings interacting with the Lesser Antilles in the Eastern Caribbean Sea. Since the passages of the Lesser Antilles have values of 0.07 ? G/d ? 0.3, the oceanic observations might be explained by the experimental results reported in this paper.