He won an 1875 match in Saint Petersburg against Russian master Ilya Shumov, 5–2.

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.

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.

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.