Date: November 19, 1999
Venue: Tokyo Bay NK Hall
City: Tokyo, Japan
- UFC Japan Middleweight Tournament Semifinals: Katsuhisa Fujii vs. Masutatsu Yano
- Fuji wins by TKO (referee stoppage due to strikes) at 3:14 of the second round.
- UFC Japan Middleweight Tournament Semifinals: Kenichi Yamamoto vs. Daiju Takase
- Yamamoto wins by unanimous decision at 15:00.
- Middleweight bout: Eugene Jackson vs. Keiichiro Yamamiya
- Jackson wins by KO at 3:12 of the third round.
- Middleweight bout: Joe Slick vs. Jason Delucia
- Slick wins by TKO (verbal submission due to knee injury) at 1:28 of the first round.
- UFC Japan Middleweight Tournament Finals: Kenichi Yamamoto vs. Katsuhisa Fujii
- Yamamoto wins the UFC Japan Middleweight Tournament by submission (kneebar) at 4:15 of the second round.
- Heavyweight bout: Pedro Rizzo vs. Tsuyoshi Kosaka
- Rizzo wins by TKO (referee stoppage due to strikes) at 1:17 of the third round.
- Heavyweight Championship bout: Kevin Randleman vs. Pete Williams
- Randleman wins by unanimous decision at 5:00 of the fifth round to claim the vacant UFC Heavyweight title.
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