The harsh and demanding roads of the Island in the first Rali Vinho da Madeira editions challenged the drivers with multiple difficulties in order to achieve average speed, impossible at a time when this type of competition was regular and was decided by the minimum penalties. Recently, a very technical asphalt did not reduce the level of success in a competition that also demands perfect knowledge of roads that impose perfect trajectories. Being so, there was an idea that it would almost be impossible for a driver to win his first competition. As a contrast of such idea, nine foreign drivers already won their premier in the competition in Madeira. Such conquests were achieved by the French Jean-Pierre Nicolas, in 1967 with a Renault R8 Gordini, by the Finnish Ari Vatanen, in a Ford Escort RS in 1978, by the Italian Toni Fassina, with the powerful Lancia Stratos em 1979, by the Luxembourgish Ali Kridel, in  1981 behind the wheel of a Ford Escort RS, by the Italian Massimo Biasion, in 1983 with a Lancia Rally 037, by the Finnish Henri Toivonen, in the following year, driving a Porsche 911 SC, by the Spanish Salvador Serviá, in 1985 with a Lancia Rally 037, by the Italian Fabrizio Tabaton, in 1986 with the very insightful Lancia Delta S4, and again in 1992, also by the Italian Andrea Aghini, driving a Lancia Delta Integrale 16V. 
In 2021 the Rali Vinho da Madeira will have, as debuts, the Spanish Jan Solans, driving a Citroën C3 Rally2, and Francisco Santana Castro in a less recent Opel Corsa B Kit-Car.