Magic: The Gathering Pro Tour season 1998–99
| Pro Player of the Year |
 Kai Budde
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| Rookie of the Year |
Dirk Baberowski
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| World Champion |
Kai Budde
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| Pro Tours | 5 | ||
| Grands Prix | 14 | ||
| Start of season | 5 September 1998 | ||
| End of season | 8 August 1999 | ||
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The 1998–99 Pro Tour season was the fourth season of the Magic: The Gathering Pro Tour. It began on 5 September 1998 with Grand Prix Boston and ended on 8 August 1999 with the conclusion of 1999 World Championship in Tokyo. The season consisted of fourteen Grand Prix, and five Pro Tours, located in Chicago, Rome, Los Angeles, New York, and Tokyo. At the end of the season Kai Budde from Germany was awarded the Pro Player of the year title.
As in the previous season a rookie won the inaugural Pro Tour. In the finals Dirk Baberowski defeated Casey McCarrel. Jon Finkel also had another final eight showing, his third in a row.
Prize pool: $151,635
Players: 324
Format: Tempest Booster Draft (Tempest-Stronghold-Exodus)
Head Judge: Charlie Catino
Pro Tour Chicago also had Top 8 loser's bracket, that had matches held as best of three instead of five. The first round paired the quarter-finals losers against each other. Finkel defeated Coene 2–1 and Fuller defeated Cedercrantz 2–0. In the second and final round the winners of the first round were paired against the losers of the Top 8 semi-finals. Fung defeated Finkel 2–1 and Klauser defeated Fuller 2–1.
Tommi Hovi won Pro Tour Rome, thus becoming the first player to win two Pro Tours. Reportedly Hovi was particularly happy to win another Pro Tour, because he won his first due to a disqualification, and thus felt it was not a proper victory. Olle Råde became the first player to have five Top 8 appearances.
Prize pool: $151,635
Players: 266
Format: Extended
Head Judge: Carl Crook
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