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.

Grand Prix – Boston, Lisbon

Pro Tour – Chicago (25–27 September 1998)

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.

Tournament data

Prize pool: $151,635 Players: 324 Format: Tempest Booster Draft (Tempest-Stronghold-Exodus) Head Judge: Charlie Catino

Top 8

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.

Final standings

Grand Prix – Austin, Birmingham

Pro Tour – Rome (13–15 November 1998)

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.

Tournament data

Prize pool: $151,635 Players: 266 Format: Extended Head Judge: Carl Crook

Top 8

The first round of the loser's bracket paired the quarter-finals losers against each other. Le Pine defeated Lauer 2–0 and Gary defeated Konstanczer 2–1. In the second and final round of the loser's bracket the winners of the first round were paired against the losers of the Top 8 semi-finals. Dato defeated Gary 2–1 and Le Pine defeated Råde 2–1.

Final standings

Grand Prix – Manila, Kyoto, San Francisco, Barcelona

Pro Tour – Los Angeles (26–28 February 1999)

Steven O'Mahoney-Schwartz won Pro Tour Los Angeles defeating his friend and fellow New Yorker Jon Finkel in the final.

Tournament data

Prize pool: $151,635 Players: 337 Format: Urza's Saga Rochester Draft (Urza's Saga) Head Judge: Charlie Catino

Top 8

Final standings

Grand Prix – Vienna, Kansas City, Oslo, Taipei

Pro Tour – New York (30 April – 2 May 1999)

In the finals of Pro Tour New York Casey McCarrel defeated Shawn Keller, both playing nearly identical decks, which was designed by Ben Rubin, Lan D. Ho, and Terry Tsang, who also made the Top 8 with the deck. The concept of their decks was to quickly generate huge amounts of mana to play big spells. Rob Dougherty and David Humpherys played nearly identical decks, designed by YMG.

Tournament data

Prize pool: $151,635 Players: 308 Format: Urza's Saga Block Constructed (Urza's Saga, Urza's Legacy) Head Judge: Dan Gray

Top 8

Final standings

Grand Prix – Amsterdam, Washington D.C.

1999 World Championships – Yokohama (4–8 August 1999)

Kai Budde won the 1999 World Championship, defeating Mark Le Pine in the finals. The match went into the books as the shortest individual Pro Tour final ever, taking about 20 minutes. The title allowed Budde to take the Pro Player of the year title as well. The United States defeated Germany in the team finals to win the national team title.

Tournament data

Prize pool: $250,000 Players: 208 Individual formats: Urza's Saga Rochester Draft (Urza's Saga-Urza's Legacy-Urza's Destiny), Standard, Extended Team formats: Team Sealed (Urza's Saga-Urza's Legacy-Urza's Destiny) – Swiss; Standard – Finals Head Judge: Charlie Catino

Top 8

Final standings

National team competition

Pro Player of the year final standings

After the World Championship Kai Budde was awarded the Pro Player of the year title.