The impact of two tubercle leading-edge (TLE) modifications on the turbulent wake of a reference marine rudder at Reynolds number 2.26 × 106 was analysed numerically using Detached Eddy Simulations (DES). This paper studies the counter-rotating vortex pair formation around the TLE and their impact on the wake structures behind the rudder to find out if the vortex interaction can accelerate the tip vortex dissipation. According to the results, the tubercles enhanced lift for angles of attack (AOA) 10º and above, but at the cost of a drag penalty which reduced the rudders’ lift-to-drag ratio. The formation of the distinctive stream-wise counter-rotating vortex pairs occurred behind the tubercles, which then interacted with the dominant tip vortex. Due to the inherent spanwise flow component of finite-span lifting surfaces the counter-rotating vortex pairs were generated at unequal strength and soon merged into singular vortices co-rotating with the tip vortex. The vortices facilitated flow compartmentalisation over the rudder suction side which broke up the trailing-edge vortex sheet and confined the spanwise flow separation over the rudder surface as AOA increased. The tubercles confined flow separation closer to the rudder tip which reduced the lift generation in the tip area and minimised the initial tip vortex strength. Large elements of stream-wise counter-rotating vorticity formed around the localised stall cells of the TLE rudders that interacted with the tip vortex downstream, introducing elliptical instabilities further weakening the tip vortex and changing its trajectory.