The Taganrog Chekhov Drama Theater was established in 1827 and was subsidized by the City Council since 1828. The first group of Russian drama artists was directed by Valentin Petrovsky and toured around the region, giving performances in Rostov, Novocherkassk, Bahmut. The repertoire consisted mainly of dramas, melodramas and vaudevilles.

Since 1863, Italian opera regularly performed in Taganrog. In 1865 a stock company to finance the construction of the new theater building was created. Forty-five thousand silver rubles of stocks were issued for the total budget of 55,000 rubles. In 1866, Taganrog established its very own Italian opera in a new opera theater building by the project of the architect Londeron from Odessa. The interiors of the theater were designed after the image of La Scala opera house in Milan, Italy. The repertoire of that time included Giuseppe Verdi, Gioacchino Antonio Rossini, Jacques Offenbach, Vincenzo Bellini, Mikhail Glinka, Pyotr Tchaikovsky and others.

In 1874, municipality acquired the theater building by the purchase of its stocks. The newly established theater commission decided to dissolve the Italian opera company in 1875 for commercial reasons. One of Taganrog Italian opera's directors and choirmasters, Gaetano Molla, stayed in Taganrog after the opera company was closed and contributed to promotion and development of music culture in this city.

Anton Chekhov was in love with theater and literature from his childhood. The first performance that he attended was Offenbach's operetta "Elena the Beautiful" onstage Taganrog City Theater on October 4, 1873. Anton was a thirteen years old Gymnasium student, and from that moment on, he became a great theater lover and used to spend on it virtually all of his savings. His favorite seat in the theater was at the back gallery for it was cheap (40 silver kopecks), and because Gymnasium students needed a special authorization to go into the theater. The permission was given not often and mostly for the weekends. Sometimes, Anton Chekhov and other fellow students disguised themselves and even wore some makeup, spectacles or a fake beard, trying to fool the regular school staff, which checked for unauthorized presence of students.

In 1901, the first movie was shown onstage Taganrog City Theater.

In 1935, during the 75th Anniversary Celebrations of Anton Chekhov, the famous artists of the Moscow Art Theater performed onstage of Taganrog Theater: Olga Knipper, Tarasova, Vishnevskaya, Moskvin and others.

In 1944, the Soviet of People's Commissars of USSR named the Taganrog City Theater after Anton Pavlovich Chekhov.

In 1960, the artists of Taganrog Chekhov Drama Theater performed onstage of the Kremlin Palace of Congress in Moscow within the framework of the centennial celebrations of Anton Chekhov's birthday.

During more than 170 years of its history, the Taganrog Chekhov Drama Theater remains the truly Russian drama theater.