1999–2000 Pro Tour season| Pro Player of the Year | Bob Maher, Jr. |
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| Rookie of the Year | Brian Davis |
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| World Champion | Jon Finkel |
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| Pro Tours | 6 |
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| Grands Prix | 20 |
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| Start of season | 3 September 1999 |
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| End of season | 6 August 2000 |
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The 1999–2000 Pro Tour season was the fifth season of the Magic: The Gathering Pro Tour. It began on 3 September 1999 with Pro Tour Boston and ended on 6 August 2000 with the conclusion of 2000 World Championship in Brussels. The season consisted of twenty Grand Prixs, and six Pro Tours, located in Washington D.C., London, Chicago, Los Angeles, New York, and Brussels. At the end of the season Bob Maher, Jr. was awarded the Pro Player of the year title.