The play opened on 17 January 1904, the director's birthday, at the Moscow Art Theatre under the direction of the actor-director Konstantin Stanislavski. During rehearsals, the structure of Act Two was re-written. Famously contrary to Chekhov's wishes, Stanislavski's version was, by and large, a tragedy. Chekhov disliked the Stanislavski production intensely, concluding that Stanislavski had "ruined" his play. In one of many letters on the subject, Chekhov would complain, "Anya, I fear, should not have any sort of tearful tone... Not once does my Anya cry, nowhere do I speak of a tearful tone, in the second act there are tears in their eyes, but the tone is happy, lively. Why did you speak in your telegram about so many tears in my play? Where are they? ... Often you will find the words "through tears," but I am describing only the expression on their faces, not tears. And in the second act there is no graveyard." The playwright's wife Olga Knipper played Madame Ranevskaya in the original Moscow Art Theatre production, as well as in the 300th production of the play by the theatre in 1943.
Although critics at the time were divided in their response to the play, the debut of The Cherry Orchard by the Moscow Art Theatre on 17 January 1904 (Stanislavski's birthday) was a resounding theatrical success and the play was almost immediately presented in many of the important provincial cities. This success was not confined only to Russia, as the play was soon seen abroad with great acclaim as well. Shortly after the play's debut, Chekhov departed for Germany due to his worsening health, and by July 1904 he was dead.
The modest and newly urbanized audiences attending pre-revolutionary performances at S. V. Panin's People's House in Saint Petersburg reportedly cheered as the cherry orchard was felled onstage.
A production in 1925 at the Oxford Playhouse by J. B. Fagan and a production in 1934 at the Sadler's Wells Theatre in London directed by Tyrone Guthrie and translated by Hubert Butler were among the first English-language productions of the play.
A television version featuring Helen Hayes as Ranevskaya, and Susan Strasberg as Anya, directed by Daniel Petrie, was broadcast as part of the Play of the Week television series in 1959.
A Royal Shakespeare Company/BBC Television version from 1962 was directed by Michael Elliott from Michel Saint-Denis stage production. This features Peggy Ashcroft as Ranevskaya, Ian Holm as Trofimov, John Gielgud as Gayev, Judi Dench as Anya, Dorothy Tutin as and Patsy Byrne as Dunyasha. This version has been released on DVD by BBC Worldwide.
The Stratford Festival of Canada mounted productions in 1965, 1987 and 1998. The 1965 production was in fact the first time that a Chekhov play had been performed there. Furthermore, The Cherry Orchard marked the Stratford directorial debut of John Hirsch. Three of the original Stratford company members were in the cast: William Hutt, playing Gaev; Douglas Campbell, as Lopahin; and William Needles, in the role of Yepihodov; and three women who are considered among the pre-eminent actors Canada has produced: Frances Hyland (Varya), Kate Reid (Ranevskaya), and Martha Henry (Dunyasha). Also in the cast were Powys Thomas (Fiers); Mervyn Blake (Pishtchik); and Mary Savidge (Charlotta), and Canadian born and trained actors: Bruno Gerussi (Yasha); Hugh Webster (Trofimov); and Susan Ringwood (Anya). 
A production starring Irene Worth as Ranevskaya, Raul Julia as Lopakhin, Mary Beth Hurt as Anya and Meryl Streep as Dunyasha, directed by Andrei Şerban and featuring Tony Award-winning costumes and set by Santo Loquasto, opened at the Lincoln Center for the Performing Arts in 1977.
A production directed by Peter Hall, translated by Michael Frayn and starring Dorothy Tutin as Ranevskaya, Albert Finney as Lopakhin, Ben Kingsley as Trofimov and Ralph Richardson as Firs, appeared at the Royal National Theatre in London in 1978 to nearly universal acclaim. A minimalist production directed by Peter Gill opened at the Riverside Studios in London also in 1978, to good reviews.
In 1981, Peter Brook mounted a production in French (La Cérisaie) with an international cast including Brook's wife Natasha Parry as Ranevskaya, Niels Arestrup as Lopakhin, and Michel Piccoli as Gayev. The production was remounted at the Brooklyn Academy of Music in 1988 after tours through Africa and the Middle East.
Also in 1981, the BBC produced a version for British television by Trevor Griffiths from a translation by Helen Rappaport and directed by Richard Eyre. Instead of her 1962 BBC role as daughter Anya, Judi Dench here played the mother Ranevskaya to Bill Paterson's Lopakhin, Anton Lesser as Trofimov, Frederick Treves as Gayev, Anna Massey as Charlotta, and a 24-year-old Timothy Spall as Yepikhodov.
The Stratford Festival’s 1987 production also used the Trevor Griffiths text, and subtly shifted the play's emphasis from Madame Ranyevskaya's economic demise to the ascent of Lopakhin. James Blendick as Lopakhin was praised for his skillful man-on-the-rise performance. The 1998 Festival production, directed by Diana Leblanc, was based on a new translation by American-born / Canadian playwright John Murell. Among its cast was Martha Henry (Ranevskaya), Stephen Russell (Leonid), Anne Ross (Anya) and Sarah Dodd (Varya). Variety noted that: “Leblanc has...remembered that this is a tragicomedy...avoided the obvious and encouraged her actors to find humor rather than high drama. It works beautifully because there is drama aplenty in merely playing these characters with integrity.” 
A film version starring Charlotte Rampling as Ranevskaya, Alan Bates as Gayev, Owen Teale as Lopakhin, Melanie Lynskey as Dunyasha and Gerard Butler as Yasha, directed by Michael Cacoyannis, appeared in 1999.
An L.A. Theatre Works recorded version of the play was produced in 2002 starring Marsha Mason, Charles Durning, Hector Elizondo, and Jennifer Tilly. Others in the cast were Jordan Baker, Jon Chardiet, Michael Cristofer, Tim DeKay, Jeffrey Jones, Christy Keef, Amy Pietz, and Joey Slotnick.
Wekande Walauwa, 2002, a Sinhalese film adapted to Sri Lankan family context was directed by the prominent Sri Lankan director Lester James Peries.
The Steppenwolf Theatre Company (Chicago, Illinois) performed a version that was translated by its Associate Artistic Director, Curt Columbus, and directed by ensemble member Tina Landau. The play premiered on 4 November 2004 and ran until 5 March 2005 at the Upstairs Theatre. Appearing in the performance were Robert Breuler, Francis Guinan, Amy Morton, Yasen Peyankov, Rondi Reed, Anne Adams, Guy Adkins, Chaon Cross, Leonard Kraft, Julian Martinez, Ned Noyes, Elizabeth Rich, Ben Viccellio, and Chris Yonan.
The Atlantic Theatre Company (New York City) in 2005 produced a new adaptation of The Cherry Orchard by Tom Donaghy, where much more of the comedy was present as the playwright had originally intended.
A new production of the play starring Annette Bening as Ranevskaya and Alfred Molina as Lopakhin, translated by Martin Sherman and directed by Sean Mathias, opened at the Mark Taper Forum in Los Angeles in February 2006.
The Huntington Theatre Company at Boston University produced a version in January 2007 using Richard Nelson's translation, directed by Nicholas Martin with Kate Burton as Madame Ranevskaya, Joyce Van Patten as Charlotta Ivanovna, and Dick Latessa as Firs.
Jonathan Miller directed the play in March–April 2007 at the Crucible Theatre, Sheffield, England. The play represents Miller's return to the British stage after nearly a decade away and stars Joanna Lumley as Ranevskaya.
Libby Appel adapted and directed the play in 2007 for her farewell season as artistic director of the Oregon Shakespeare Festival (Ashland, Oregon). The new translation, based on an original literal translation by Allison Horsley, is considered to be "strongly Americanized".
A version of the play was performed as the opening production on the Chichester Festival Theatre Stage in May–June 2008, with a cast including Dame Diana Rigg, Frank Finlay, Natalie Cassidy, Jemma Redgrave and Maureen Lipman.
In 2009, a new version of the play by Tom Stoppard was performed as the first production of The Bridge Project, a partnership between North American and UK theatres. The play ran at the Brooklyn Academy of Music. Sam Mendes directed the production with a cast including Simon Russell Beale, Sinéad Cusack, Richard Easton, Rebecca Hall and Ethan Hawke.
A brand new adaptation of the play was produced by the Blackeyed Theatre in spring 2009 as a UK tour, with a cast of four.
In September 2009, a new adaptation of the play by Stuart Paterson was produced at the Dundee Repertory Theatre with guest director Vladimir Bouchler.
A new translation of the play in Punjabi was performed in September 2009 by the students of Theatre Art Department of Punjabi University, Patiala, India.
A version of the play in Afrikaans was performed in late September 2009 by students of the Department of Drama at the University of Cape Town, South Africa.
A new adaption was commissioned by the Brighton Festival and performed by the dreamthinkspeak group. They renovated the old co-op home-store on the London Road using the whole store as a stage. They renamed it Before I Sleep and said it was inspired by the original play. It received positive reviews from both The Guardian and The Independent newspapers. It was funded by Arts Council England, National Lottery and a long list of other Brighton and Hove based businesses.
In April 2010 at the Royal Lyceum Theatre in Edinburgh the Scottish playwright John Byrne staged a new version of the play as a Scottish 'social comedy', taking place in 1979 Scotland.
The Royal National Theatre in London staged a new version starring Zoë Wanamaker from May to August 2011, reuniting director Howard Davies with writer Andrew Upton, which was also shown at cinemas internationally through National Theatre Live.
The Eastern Bohemian Theatre, Pardubice, Czech Republic. Directed by Petr Novotný (director). Translated by Leoš Suchařípa. Starring: Jindra Janoušková (Ranevskaya), Petra Tenorová (Anya), Kristina Jelínková (Varya), Zdeněk Rumpík (Gayev), Jiří Kalužný (Lopakhin), Miloslav Tichý (Trofimov), Martin Mejzlík (Simeonov-Pishchik), Lída Vlášková (Charlotte), Ladislav Špiner (Yepikhodov), Martina Sikorová (Dunyasha), Václav Dušek (Firs), Jan Musil (Yasha), Radek Žák (Stationmaster), Alexandr Postler (Stranger). The play had a premiere 16 and 17 October 2011 at 7 pm and last performance on 14 January 2012.
The Vinohrady Theatre, Prague. Directed by Vladimír Morávek. Starring Dagmar Veškrnová-Havlová, Jiřina Jirásková (Charlotte), Viktor Preiss, Pavla Tomicová, Martin Stropnický, Lucie Juřičková, Svatopluk Skopal, Andrea Elsnerová, Pavel Batěk, Ilja Racek, Martin Zahálka, Jiří Dvořák, jiří Žák. The play had its premiere on 5 February 2008.
The Komorní scéna Aréna, Ostrava. Directed by Ivan Krejčí. Starring Alena Sasínová-Polarczyk, Tereza Dočkalová, Petra Kocmanová, Norbert Lichý, Josef Kaluža, Michal Čapka, Dušan Škubal, Dana Fialková, Michal Moučka, Tereza Cisovská, Pavel Cisovský, Albert Čuba, Marek Cisovský, René Šmotek. The play had premiere on 21 March 2009.
The Theatre Workshop of Nantucket staged a new adaptation and translation of Chekhov's Cherry Orchard set on Nantucket in 1972. The play premiered on 14 September 2012. It was directed by Anne Breeding and Gregory Stroud, and translated and adapted by Gregory Stroud.
The Stage Center Theatre at Northeastern Illinois University, Chicago, Illinois, presented a new version of The Cherry Orchard, adapted and directed by Dan Wirth, in October, 2013.
PK Productions will premiere a new version of The Cherry Orchard in November 2014 at the New Wimbledon Theatre. Adapted by director Patrick Kennedy, the production updates the setting to London in 1976.
Directed by Katie Mitchell, The Cherry Orchard opened at The Young Vic Theatre in London on 10 October 2014
A production of the Michael Frayn translation is in production at Helmsley Arts Centre in Helmsley, North Yorkshire in May 2015, directed by David Powley.
Clemence Williams directed New Theatre (Sydney) production of David Mamet's adaptation 26 April – 28 May 2016 with an original musical score by Eliza Scott.
Roundabout Theatre Company presented a new adaptation by Stephen Karam on Broadway at the American Airlines Theatre, starring Diane Lane as Ranevskaya. Previews began on 15 September 2016, with opening night on 16 October. The production was directed by Simon Godwin, with scenic design by Scott Pask, costume design by Michael Krass, lighting design by Donald Holder, sound design by Christopher Cronin, movement by Jonathan Goddard, and original music by Nico Muhly.
During its 2018 season, Shaw Festival in Niagara-on-the Lake, Ontario presented a world premiere of The Orchard (after Chekov).  Described as The Cherry Orchard transformed into the tale of a Punjabi-Sikh family fighting to hold onto their Okanagan Valley orchard, this version is based on the author Sarena Parmar’s own childhood in British Columbia. “This fresh adaptation confronts life, loss and the Canadian immigrant experience with both bravery and beauty...” It will go on to be produced at the Arts Club in Vancouver, B.C. in April 2019.
A new radio version by Katherine Tozer and composer John Chambers was produced for BBC's Drama on 3, airing for the first time on 18 October 2018.
The Moscow Pushkin Drama Theatre will be presenting their adaptation of the play with the Cherry Orchard Festival at the New York City Center in June 2020. Directed by Vladimir Mirzoev, and starring Victoria Isakova, Aleksander Petrov, Mikhail Zhigalov, and Maxim Vitorgan, and has been described as, "Visually striking, psychologically nuanced and hypnotically performed Russian staging of Chekhov's play"