Born in Ufa, Soviet Union, Cherkasov first came to the tennis world's attention as an outstanding junior player. In 1987, he was ranked the World No. 3 junior player and finished runner-up in the boys' singles at the US Open (lost to David Wheaton in the final).

Cherkasov turned professional in 1988. In 1990, Cherkasov claimed his first top-level singles titles when he won the inaugural Kremlin Cup in Moscow, defeating Tim Mayotte in the final 6–2, 6–1. He also reached the quarter-finals of the 1990 Australian Open and US Open.

In June 1991 Cherkasov reached his career-high singles ranking of World No. 13. In November he successfully defended his Kremlin Cup title, saving two match points in a 7–6, 3–6, 7–6 win in the final against Jakob Hlasek.

In 1992, Cherkasov was a quarter-finalist at the French Open and won a men's singles bronze medal at the Olympic Games in Barcelona, notably rallying from 2 sets down to beat Pete Sampras in the third round.

In 1993, Cherkasov saved three match points in 3-hour, 54-minute quarter-final victory over Italy's Andrea Gaudenzi at Tel Aviv, to win 6–7, 7–6, 7–5 in what was the longest best-of-three set match in tour history.

In the end, his two victories at the Kremlin Cup in Moscow proved to be the only top-level titles of Cherkasov's career. He retired from the professional tour in 2000, having earned prize-money totalling $2,259,875.

ATP career finals

Singles: 6 (2 titles, 4 runner-ups)

Legend
Grand Slam Tournaments (0–0)
ATP World Tour Finals (0–0)
ATP Masters 1000 Series (0–0)
ATP 500 Series (0–1)
ATP 250 Series (2–3)

Finals by surface
Hard (0–1)
Clay (0–2)
Grass (0–0)
Carpet (2–1)

Finals by setting
Outdoors (0–3)
Indoors (2–1)

Result	W–L	Date	Tournament	Tier	Surface	Opponent	Score
Loss	0–1	Jan 1989	Sydney, Australia	Grand Prix	Hard	Aaron Krickstein	4–6, 2–6
Win	1–1	Nov 1990	Moscow, USSR	Grand Prix	Carpet	Tim Mayotte	6–2, 6–1
Loss	1–2	Feb 1991	Brussels, Belgium	Championship Series	Carpet	Guy Forget	3–6, 5–7, 6–3, 6–7^(4–7)
Win	2–2	Nov 1991	Moscow, USSR	World Series	Carpet	Jakob Hlasek	7–6^(7–2), 3–6, 7–6^(7–5)
Loss	2–3	May 1993	Bologna, Italy	World Series	Clay	Jordi Burillo	6–7^(4–7), 7–6^(9–7), 1–6
Loss	2–4	Sep 1993	Bucharest, Romania	World Series	Clay	Goran Ivanišević	2–6, 6–7^(5–7)

Doubles: 2 (2 runners-up)

Legend
Grand Slam Tournaments (0–0)
ATP World Tour Finals (0–0)
ATP Masters Series (0–0)
ATP Championship Series (0–0)
ATP World Series (0–2)

Finals by surface
Hard (0–0)
Clay (0–1)
Grass (0–0)
Carpet (0–1)

Finals by setting
Outdoors (0–1)
Indoors (0–1)

Result	W–L	Date	Tournament	Tier	Surface	Partner	Opponents	Score
Loss	0–1	May 1990	Umag, Croatia	World Series	Clay	Andrei Olhovskiy	Vojtech Flegl Daniel Vacek	4–6, 4–6
Loss	0–2	Nov 1991	Moscow, USSR	World Series	Carpet	Alexander Volkov	Eric Jelen Carl-Uwe Steeb	4–6, 6–7

ATP Challenger and ITF Futures finals

Singles: 9 (5–4)

Legend
ATP Challenger (4–2)
ITF Futures (1–2)

Finals by surface
Hard (3–0)
Clay (2–4)
Grass (0–0)
Carpet (0–0)

Result	W–L	Date	Tournament	Tier	Surface	Opponent	Score
Win	1-0	Apr 1989	Oporto, Portugal	Challenger	Clay	Javier Sánchez	7–6, 7–5
Win	2-0	Apr 1989	Lisbon, Portugal	Challenger	Clay	Tomas Carbonell	7–6, 6–3
Loss	2-1	May 1993	Ljubljana, Slovenia	Challenger	Clay	Daniel Orsanic	6–4, 2–6, 5–7
Win	3-1	Sep 1995	Singapore, Singapore	Challenger	Hard	Yasufumi Yamamoto	6–1, 6–3
Win	4-1	Dec 1996	Daytona Beach, United States	Challenger	Hard	Tommy Haas	7–6, 3–6, 7–5
Loss	4-2	Aug 1998	Warsaw, Poland	Challenger	Clay	Jiri Vanek	6–7, 5–7
Win	5-2	Apr 2001	USA F9, Stone Mountain	Futures	Hard	Robert Kendrick	6–1, 6–1
Loss	5-3	Jul 2002	Denmark F1, Copenhagen	Futures	Clay	Edouard Roger-Vasselin	2–6, 3–6
Loss	5-4	Aug 2002	Latvia F1, Jūrmala	Futures	Clay	Timo Nieminen	6–4, 4–6, 2–6

Doubles: 7 (3–4)

Legend
ATP Challenger (2–3)
ITF Futures (1–1)

Finals by surface
Hard (3–0)
Clay (0–4)
Grass (0–0)
Carpet (0–0)

Result	W–L	Date	Tournament	Tier	Surface	Partner	Opponents	Score
Loss	0–1	Sep 1996	Tashkent, Uzbekistan	Challenger	Clay	Laurence Tieleman	Marcelo Charpentier Albert Portas	1–6, 2–6
Win	1–1	Sep 1997	Azores, Portugal	Challenger	Hard	Gaston Etlis	Nils Holm Lars-Anders Wahlgren	6–7, 7–5, 6–3
Win	2–1	Dec 1997	Eilat, Israel	Challenger	Hard	Patrick Baur	Sander Groen Rogier Wassen	6–3, 7–6
Loss	2–2	Apr 1998	Paget, Bermuda	Challenger	Clay	Rodolphe Gilbert	Doug Flach Richey Reneberg	6–3, 4–6, 2–6
Loss	2–3	Aug 1999	Poznan, Poland	Challenger	Clay	Hugo Armando	Massimo Ardinghi Davide Sanguinetti	4–6, 4–6
Loss	2–4	Aug 2002	Latvia F1, Jūrmala	Futures	Clay	Dmitri Kotchetkov	Aleksander Jerinkic Steven Randjelovic	3–6, 1–6
Win	3–4	Jun 2004	Spain F11, Lanzarote	Futures	Hard	Orest Tereshchuk	Jaymon Crabb Brodie Stewart	6–3, 4–6, 6–3

Junior Grand Slam finals

Singles: 1 (1 runner-up)

Result	Year	Tournament	Surface	Opponent	Score
Loss	1987	US Open	Hard	David Wheaton	5–7, 0–6

Performance timeline

**Key**
W	F	SF	QF	#R	RR	Q#	DNQ	A	NH

(W) winner; (F) finalist; (SF) semifinalist; (QF) quarterfinalist; (#R) rounds 4, 3, 2, 1; (RR) round-robin stage; (Q#) qualification round; (DNQ) did not qualify; (A) absent; (NH) not held; (SR) strike rate (events won / competed); (W–L) win–loss record.

Singles

Tournament	1988	1989	1990	1991	1992	1993	1994	1995	1996	1997	1998	1999	2000	2001	SR	W–L	Win %
Grand Slam tournaments
Australian Open	A	A	QF	2R	2R	1R	2R	A	1R	1R	Q1	2R	Q2	A	0 / 8	8–8	50%
French Open	A	2R	2R	4R	QF	1R	1R	Q1	Q2	Q2	Q1	Q2	Q1	Q1	0 / 6	9–6	60%
Wimbledon	Q1	1R	1R	1R	1R	1R	1R	A	A	A	A	A	A	A	0 / 6	0–6	0%
US Open	A	1R	QF	1R	1R	1R	1R	A	A	A	A	Q2	Q1	A	0 / 6	4–6	40%
Win–loss	0–0	1–3	9–4	4–4	5–4	0–4	1–4	0–0	0–1	0–1	0–0	1–1	0–0	0–0	0 / 26	21–26	45%
Olympic Games
Summer Olympics	2R	Not Held			SF	Not Held			A	Not Held			A	NH	0 / 2	5–2	71%
ATP Masters Series
Indian Wells	A	A	A	3R	QF	1R	1R	A	Q2	A	A	A	A	A	0 / 4	5–4	56%
Miami	A	A	1R	2R	QF	2R	3R	A	A	A	1R	Q1	A	A	0 / 6	4–6	40%
Monte Carlo	A	A	A	3R	1R	3R	1R	Q2	1R	Q2	A	Q2	A	A	0 / 5	4–5	44%
Hamburg	A	2R	3R	2R	2R	A	1R	1R	A	Q1	Q1	Q2	A	A	0 / 6	5–6	45%
Rome	A	A	A	QF	2R	1R	1R	A	A	A	A	A	A	A	0 / 4	4–4	50%
Cincinnati	A	1R	A	QF	2R	2R	2R	A	A	A	A	A	A	A	0 / 5	6–5	55%
Paris	A	A	2R	2R	1R	2R	A	Q3	A	Q2	A	A	A	A	0 / 4	3–4	43%
Win–loss	0–0	1–2	3–3	12–7	9–7	4–6	2–6	0–1	0–1	0–0	0–1	0–0	0–0	0–0	0- / 34	31–34	48%

Career