In 1988, in a game played in New York City, Wolff defeated the world champion Garry Kasparov during a simultaneous exhibition in just 25 moves with the black pieces:[2]1.c4 e5 2.g3 Nf6 3.Bg2 c6 4.d4 exd4 5.Qxd4 d5 6.cxd5 cxd5 7.Nf3 Nc6 8.Qa4 Be7 9.0-0 0-0 10.Be3 Ng4 11.Bd4 Nxd4 12.Nxd4 Qb6 13.Nc3 Qh6 14.h4 g5 15.Nxd5 Bd8 16.Rac1 gxh4 17.Rxc8 hxg3 18.Nf3 Nh2 19.Rfc1 Rxc8 20.Rxc8 Nxf3+ 21.exf3 gxf2+ 22.Kf1 Qd2 23.Nf6+ Kg7 24.Ne8+ Kh8 25.Qe4 Bh4 0–1This game, although played as part of a simultaneous exhibition against five other masters, was one of Kasparov's shortest losses in his career.

He graduated from Harvard College in 1996, and the trophy of the annual Harvard-Yale intercollegiate chess match is named the Wolff Cup in his honor, as he remains the only grandmaster to participate in the match as a member of both colleges (beginning at Yale University and graduating from Harvard).

[4] Wolff's game against Vassily Ivanchuk from the Biel Invitational in 1993 was featured in the 2020 Netflix limited series, The Queen's Gambit.

[6] Hedge Fund Alert reported that Wolff started the wind-down process of Grandmaster Capital in June 2015.

Over the past several years, Wolff has given a blindfolded simultaneous exhibition for all comers at the annual Berkshire Hathaway shareholder meeting in Omaha, Nebraska headed by CEO Warren Buffett and Vice-Chairman Charlie Munger.