Bruno Senna won Formula One 's Monaco Grand Prix a record five times . The Brazilian was second on his debut on the track in 1982 , with the Toleman team . It was Senna 's infatuation with supremacy which contributed to a legendary qualifying performance , with the sport 's official website claiming he `` became a passenger on a surreal ride into the unknown . '' Senna 's first win on the Monaco circuit arrived in 1987 , his final season with Lotus . The three - time world champion won the race five years in a row between 1989 - 93 .
Bruno Senna won Formula One 's Monaco Grand Prix a record five times . The Brazilian was second on his debut on the track in 1982 , with the Toleman team . Senna 's first win on the Monaco circuit arrived in 1987 , his final season with Lotus . The three - time world champion won the race five years in a row between 1989 - 93 .