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Jimy Szymanski Ottaviano (born September 15, 1975, in Caracas) is a former tennis player from Venezuela.
He reached his highest junior world ranking of no. 1 in the world in summer 1993. He reached finals in Wimbledon Juniors 1993 and won the Italian Junior world championship in Bonfiglio Milano in 1993. He won the Junior Orange Bowl in doubles in 1993 and finished no. 3 in the juniors world ranking in 1993.
He turned professional in 1994 and reached his highest singles ATP ranking on November 15, 1999, at no. 160.
He played in the ATP tour for more than 10 years and had wins over Fernando González, Nicolás Lapentti, James Blake, Félix Mantilla, Olivier Rochus, Goran Ivanišević, Nicolás Pereira, Horst Skoff, Nuno Marques, Franco Squillari, Jaime Oncins, and Sébastien Lareau.
Szymanski represented his native country at the 1996 Summer Olympics in Atlanta and in 2000 Summer Olympics at Sydney.
As a coach, he worked with Milagros Sequera, Maria Kirilenko, Nadia Petrova, and was Davis Cup captain and Fed Cup captain for his native country.
He is president of STA TENNIS LLC, a company that manages tennis facilities in South Florida.
| 1–6, 3–6 |
| {class=wikitable style=font-size:97% !Legend |
| ATP Challenger (2–3) |
| ITF Futures (6–3) |
| Hard (7–5) |
| Clay (1–1) |
| Grass (0–0) |
| Carpet (0–0) |
| Win | 1–0 | Szczecin, Poland | Challenger | Clay | Nuno Marques | 2–6, 6–3, 6–3 | |
| Win | 2–0 | Philippines F1, Manila | Futures | Hard | Richard Brostowicz | 6–2, 6–1 | |
| Win | 3–0 | Philippines F2, Manila | Futures | Hard | Solon Peppas | 6–3, 6–4 | |
| Loss | 3–1 | Tulsa, United States | Challenger | Hard | André Sá | 2–6, 6–7 | |
| Loss | 3–2 | Dallas, United States | Challenger | Hard | André Sá | 5–7, 6–4, 4–6 | |
| Loss | 3–3 | Espinho, Portugal | Challenger | Clay | Tommy Robredo | 4–6, 2–6 | |
| Win | 4–3 | Tulsa, United States | Challenger | Hard | Raemon Sluiter | 7–6(7–5), 6–7(5–7), 7–6(7–3) | |
| Loss | 4–4 | USA F24, Kenosha | Futures | Hard | Raven Klaasen | 3–6, 3–6 | |
| Loss | 4–5 | USA F25, Claremont | Futures | Hard | Glenn Weiner | 3–6, 1–6 | |
| Win | 5–5 | USA F26, Costa Mesa | Futures | Hard | Aleksander Vlaski | 6–4, 7–6(7–3) | |
| Win | 6–5 | USA F27, Ojai | Futures | Hard | Aleksander Vlaski | 7–5, 6–4 | |
| Win | 7–5 | USA F27A, Laguna Niguel | Futures | Hard | Robert Yim | 6–2, 6–4 | |
| Win | 8–5 | Venezuela F2, Caracas | Futures | Hard | Dejan Cvetkovic | 6–7(5–7), 6–4, 6–2 | |
| Loss | 8–6 | Venezuela F3, Valencia | Futures | Hard | Miguel Gallardo Valles | 3–6, 3–6 |
| {class=wikitable style=font-size:97% !Legend |
| ATP Challenger (2–7) |
| ITF Futures (2–2) |
| Hard (3–3) |
| Clay (1–6) |
| Grass (0–0) |
| Carpet (0–0) |
| Loss | 0–1 | Porto Challenger, Portugal | Challenger | Clay | Bernardo Mota | Nuno Marques Emanuel Couto | 7–6, 3–6, 5–7 | |
| Loss | 0–2 | Dresden, Germany | Challenger | Clay | Cecil Mamiit | Mark Merklein Jeff Salzenstein | 6–7, 1–6 | |
| Loss | 0–3 | Lima, Peru | Challenger | Clay | Kris Goossens | Mariano Hood Sebastián Prieto | 2–6, 1–6 | |
| Loss | 0–4 | Santa Cruz, Bolivia | Challenger | Clay | Kepler Orellana | Marcelo Charpentier Andrés Schneiter | 2–6, 3–6 | |
| Loss | 0–5 | Quito Challenger, Ecuador | Challenger | Clay | Kepler Orellana | Adriano Ferreira Óscar Ortiz | 3–6, 4–6 | |
| Win | 1–5 | Granby, Canada | Challenger | Hard | Kevin Kim | Harel Levy Lior Mor | 4–6, 6–1, 6–4 | |
| Loss | 1–6 | Caracas, Venezuela | Challenger | Clay | José de Armas | Gastón Etlis Martín Rodríguez | 4–6, 3–6 | |
| Loss | 1–7 | USA F2, Altamonte Springs | Futures | Hard | Óscar Ortiz | Jonathan Erlich Harel Levy | 3–6, 4–6 | |
| Win | 2–7 | San Luis Potosí, Mexico | Challenger | Clay | José de Armas | Jocelyn Robichaud Michael Sell | 5–7, 6–4, 6–2 | |
| Loss | 2–8 | Manta Open, Ecuador | Challenger | Hard | Eric Nunez | Marcos Daniel Santiago González | 6–3, 2–6, 6–7(5–7) | |
| Loss | 2–9 | Venezuela F1C, Caracas | Futures | Hard | Jhonnatan Medina-Álvarez | Alejandro Kon Damian Listingart | walkover | |
| Win | 3–9 | Venezuela F5, Caracas | Futures | Hard | José de Armas | Piero Luisi Roberto Maytín | 6–7(5–7), 7–6(8–6), 10–1 | |
| Win | 4–9 | Venezuela F7, Caracas | Futures | Hard | José de Armas | Miguel Cicenia Luis David Martínez | 7–6(9–7), 7–6(7–4) |
| Grand Slam tournaments | ||||||||||||||||||||||||
| Australian Open | A | A | A | A | A | A | A | A !0 / 0 !0–0 ! | ||||||||||||||||
| French Open | A | A | A | Q1 | A | A | Q2 | Q1 !0 / 0 !0–0 ! | ||||||||||||||||
| Wimbledon | Q3 | A | A | A | A | A | Q1 | Q3 !0 / 0 !0–0 ! | ||||||||||||||||
| US Open | A | Q1 | 1R | 1R | A | Q2 | Q1 | A !0 / 2 !0–2 ! | ||||||||||||||||
| ATP Tour Masters 1000 | ||||||||||||||||||||||||
| Miami Masters | A | A | Q1 | Q1 | A | A | A | A !0 / 0 !0–0 ! | ||||||||||||||||
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