| 2025-01-31 | Buffalo de Bill | 208 | The Chessmaster 2000: Full game (WHITE) | 0:00 |
| 2024-10-23 |  Renaldo Lo Muto | 772 | The Chessmaster 2000 (Commodore 64 / Gameplay #0849) | 0:00 |
| 2024-09-25 |  Hundgirrid Channel | 491 | The Chessmaster 2000 - Atari ST / STE | 0:00 |
| 2023-09-30 |  Robert's Retro-Gaming | 1,540 | Atari 8-Bit Game Play, Chessmaster 2000 | 21:37 |
| 2023-08-26 |  SwiftSmash Gaming Zone | 481 | The Chessmaster 2000 Gameplay (SNES) | 10:15 |
| 2023-04-07 | A Thousand and One Adventures | 6,790 | Sfida a scacchi tra 8 bit / ZX Spectrum vs Commodore 64 | 14:13 |
| 2023-03-03 |  PlayGames | 621 | Enterprise 64 & 128 - The Chessmaster 2000 | 0:31 |
| 2023-02-27 |  La Mazmorra Abandon | 17,900 | The Chessmaster 2000 (The Software Toolworks) (MS-DOS) [1986] [PC Longplay] | 14:04 |
| 2023-02-03 |  petsasjim1 | 19,300 | ATARI ST THE CHESSMASTER 2000 By The Software Toolworks & Electronic Arts In 1986 | 3:38 |
| 2023-01-12 | Ryan FB | 914 | Moof A Day: The Chessmaster 2000 v1.02 (Macintosh, 1986) | 12:49 |
| 2022-06-24 |  UnknDoomer's corner of ultra silence | 761 | The Chessmaster 2000 (1986). Gameplay. For Old-Games.ru. 87. | 0:00 |
| 2022-05-23 |  Retro Gaming Discourse | 4,950 | Random DOS Game Show #524: Chessmaster 2000 (1986) | 7:24 |
| 2022-04-25 | Ivan Paduano | 10,500 | Game of the day 3548 The Chessmaster 2000 Electronic Arts 1986 | 9:24 |
| 2022-01-28 | Nas_Sutromi | 1,250 | Zx Spectrum 128k Real Tape: ChessMaster 2000 | 12:52 |
| 2021-12-21 | Jason Doucette | 878 | Chessmaster 2000 - First Play since childhood | 30:52 |
| 2021-11-07 | MrPetari | 456 | Chessmaster2000 MSTE | 0:47 |
| 2021-08-25 | Xadrez Brasil | 361,000 | Já jogou contra o Chessmaster 2000 dos anos 80? | 44:26 |
| 2021-03-24 |  Lipos Retro Schachcomputer | 1,020 | Mephisto Exclusiv V vs. Chessmaster 2000 | 38:38 |
| 2021-01-21 | The Video Game Museum | 10,200 | The Chessmaster 2000 © 1986 Software Toolworks - PC DOS - Gameplay | 8:45 |
| 2020-12-21 | Sven Dännart | 2,540 | Chessmaster 2000 / Atari St Version | 3:00 |
| 2020-02-04 | zxspectrumgames4 | 7,170 | The Chessmaster 2000 (DOS) | 16:02 |
| 2018-12-16 | Retro Playthrus | 424 | Chessmaster 2000 - Atari ST [022] PlayThru | 15:15 |
| 2017-04-27 | FunCade 64 (FC64) | 2,290 | Chessmaster 2000 ~ Amiga | 0:35 |
| 2015-04-25 | Squakenet | 29,600 | Chessmaster 2000 gameplay (PC Game, 1986) | 6:37 |
| 2014-07-01 | 1GO ShortPlay Retro Games | 452 | 1GO Short Play - Chessmaster 2000 (Amiga) | 3:35 |
| 2013-12-29 | Enrique G. Gálvez | 10,300 | Chessmaster 2000 (PC) | 2:02 |
