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The 1999 Monaco Grand Prix (formally the LVII Grand Prix Automobile de Monaco) was a Formula One motor race held on 16 May 1999 at the Circuit de Monaco in Monte Carlo, Monaco. It was the fourth race of the 1999 Formula One season. The 78-lap race was won by Ferrari driver Michael Schumacher after starting from second position. It was Schumacher's 16th win with Ferrari, breaking the record held by Niki Lauda. His team-mate Eddie Irvine finished second with Mika Häkkinen third for the McLaren team.
The race was Schumacher's second win of the season, his fourth at Monaco, and the result meant that he extended his lead in the Drivers' Championship, to eight points over Irvine and twelve over Häkkinen. Ferrari extended their lead in the Constructors' Championship, twenty-four points ahead of McLaren and twenty-eight ahead of Jordan with 12 races of the season remaining.