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At the Paris 1867 tournament held at the Café de la Régence, his first international tournament, Winawer finished in second place, tied with Wilhelm Steinitz behind Ignatz Von Kolisch. He remained one of the world's best players for the next 15 years.
At Warsaw 1868 Winawer won the first chess tournament conducted in Poland. He won an 1875 match in Saint Petersburg against Russian master Ilya Shumov, 5–2. At Paris 1878 Winawer tied for first place (+14−3=5) with Johannes Zukertort, ahead of Joseph Henry Blackburne and George Henry Mackenzie, but took second prize after the play-off. At Berlin 1881 he finished =3rd with Mikhail Chigorin. Winawer's best result was a first place tie with Steinitz at Vienna 1882, in what was the strongest chess tournament in history up to that time. At London 1883 he failed to place for the first time, but later that year at Nuremberg (3rd German Congress) he finished first, defeating Blackburne who took second place.
After a long absence Winawer returned to chess in the 1890s, but by then he had been surpassed by younger players including Siegbert Tarrasch and Emanuel Lasker. At Dresden 1892 and Budapest 1896 he placed sixth. He lost an 1896 match to Dawid Janowski 2–5. He turned 63 during his final international tournament, Monte Carlo 1901, and did not place among the prizewinners. Winawer continued to play competitive chess into his 60s, and in his career he faced all of the top players from the last third of the 19th century, from Adolf Anderssen to Lasker. His rivalry with Blackburne stretched from 1870 to 1901, and they met in competitive games in five consecutive decades. Winawer died in Warsaw on November 29, 1919.
Winawer has several opening variations named for him. The most popular is the Winawer Variation of the French Defence (1.e4 e6 2.d4 d5 3.Nc3 Bb4). His name is also associated with the Winawer Attack in the Ruy Lopez. <At Monte Carlo 1901, Winawer's last international tournament, he introduced the Winawer Countergambit in the Slav Defense in a game against Frank Marshall.>