Junior

Krickstein started playing tennis when he was six.^[15] He became an active competitor on the high school tennis scene during his teens, and still holds the Michigan record for most consecutive match wins at this level (56). He played for University Liggett School.^[16]

Krickstein won the American National Under 16 championship in 1982. While still only 16, he was the US National Junior Tennis Association Champion, Clay Champion, and USTA National Champion in the 18s in 1983.^[17] He won five consecutive junior championships.^[15]

Professional

Krickstein set an ATP record for being the youngest player to win a singles title on the ATP Tour (at age 16, 2 months after his 16th birthday), in Tel Aviv. Krickstein set a record for being the youngest player to ever break the top 10 (at age 17).^[2][7] As of April 2024, both records still stand.

In 1984, he won the U.S. Pro Tennis Championship, becoming its youngest winner, and a clay court tournament in Boston.^[8] In 1989 he won the Tokyo Indoor Tennis Tournament and a hard court tournament in Sydney, Australia.^[8] In 1991, 1992, and 1993 he won the South African Open.^[8]

Krickstein had an injury-plagued career, which included stress fractures in his feet, problems with his knees and wrists in 1985 and 1986, and injuries suffered when he was hurt in a car accident in 1987.^[18]

His best finishes in a Grand Slam event were at the 1989 US Open, and at the 1995 Australian Open, where he reached the semi-finals.

Krickstein is perhaps best remembered for his famous five-set match against Jimmy Connors on Labor Day at the 1991 US Open. Krickstein had led the match 2–1 in sets and was ahead 5–2 in the fifth set, before losing the match in a tiebreaker. The match lasted four hours and 41 minutes.^[19] According to ESPN, "The match was an instant classic." Before retractable roofs were constructed for use at the US Open, this match was the default television filler during tournament rain delays; because of this, it is probably the most viewed tennis match of all time.^[20] For about 24 years after the match, Krickstein and Connors only spoke a few words to each other. But in 2014, Krickstein called Connors to invite him to play a "reunion match" for members at the Florida country club where Krickstein was (and still is) the tennis director. They played in February 2015 and Krickstein won a pro set 8–5.^[21][22]

He had a record of 10 career wins from 0–2 set deficits. His nickname "Marathon Man" was a reference to his ability to make a comeback when behind in a match.^[2][23][24] Krickstein won 27 of his 35 career matches that went into a fifth set.

Krickstein defeated a number of top players, including Ivan Lendl (world #1) in 1990, Michael Stich (world #2 and #4) in 1994 and 1991, Stefan Edberg (world #3) in 1988 at the US Open, Boris Becker (world #3) in 1992, Mats Wilander (world #4) in 1984, Jimmy Arias (world #5) in 1984, and Sergi Bruguera (world #5) in 1994. He won against Pete Sampras and Andre Agassi.

Davis Cup

Krickstein was a member of the United States Davis Cup team from 1985 to 1987, and also was a member of the 1990 squad. He compiled a 6–4 record in singles play during Davis Cup ties.^[25] The highlight of Krickstein's Davis Cup career came in 1990 when he scored two, hard-fought victories in a World Group Quarterfinal tie against Czechoslovakia, leading his team to a 4–1 win.

Singles: 19 (9 titles, 10 runner-ups)

More information Result, W–L ...

Result	W–L	Date	Tournament	Tier	Surface	Opponent	Score
Win	1–0	Oct 1983	Tel Aviv, Israel	Grand Prix	Hard	Christoph Zipf	7–6, 6–3
Loss	1–1	May 1984	Rome, Italy	Grand Prix	Clay	Andrés Gómez	6–2, 1–6, 2–6, 2–6
Win	2–1	Jul 1984	Boston, United States	Grand Prix	Clay	José Luis Clerc	7–6(7–2), 3–6, 6–4
Loss	2–2	Jul 1984	Washington, United States	Grand Prix	Clay	Andrés Gómez	2–6, 2–6
Win	3–2	Sep 1984	Tel Aviv (2), Israel	Grand Prix	Hard	Shahar Perkiss	6–4, 6–1
Win	4–2	Sep 1984	Geneva, Switzerland	Grand Prix	Clay	Henrik Sundström	6–7, 6–1, 6–4
Loss	4–3	Nov 1985	Hong Kong, Hong Kong	Grand Prix	Hard	Andrés Gómez	3–6, 3–6, 6–3, 4–6
Loss	4–4	Oct 1986	Tel Aviv, Israel	Grand Prix	Hard	Brad Gilbert	5–7, 2–6
Loss	4–5	Oct 1988	Tel Aviv, Israel	Grand Prix	Hard	Brad Gilbert	6–4, 6–7(5–7), 2–6
Loss	4–6	Nov 1988	Detroit, United States	Grand Prix	Carpet	John McEnroe	5–7, 2–6
Win	5–6	Jan 1989	Sydney, Australia	Grand Prix	Hard	Andrei Cherkasov	6–4, 6–2
Win	6–6	Sep 1989	Los Angeles, United States	Grand Prix	Hard	Michael Chang	2–6, 6–4, 6–2
Win	7–6	Oct 1989	Tokyo, Japan	Grand Prix	Carpet	Carl-Uwe Steeb	6–2, 6–2
Loss	7–7	Apr 1990	Tokyo, Japan	Championship Series	Hard	Stefan Edberg	4–6, 5–7
Loss	7–8	Sep 1990	Brisbane, Australia	World Series	Hard	Brad Gilbert	3–6, 1–6
Loss	7–9	Sep 1991	Brisbane, Australia	World Series	Hard	Gianluca Pozzi	3–6, 6–7(4–7)
Win	8–9	Mar 1992	Johannesburg, South Africa	World Series	Hard	Alexander Volkov	6–4, 6–4
Loss	8–10	Apr 1992	Monte Carlo, Monaco	Masters Series	Clay	Thomas Muster	3–6, 1–6, 3–6
Win	9–10	Mar 1993	Johannesburg (2), South Africa	World Series	Hard	Grant Stafford	6–3, 7–6(9–7)

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