| 2023-09-30 |  Robert's Retro-Gaming | Atari 8-Bit Game Play, Chessmaster 2000 | 21:37 | 9 |
| 2023-08-26 |  SwiftSmash Gaming Zone | The Chessmaster 2000 Gameplay (SNES) | 10:15 | 17 |
| 2023-04-07 |  Thousand and One Adventure | Sfida a scacchi tra 8 bit / ZX Spectrum vs Commodore 64 | 14:13 | 238 |
| 2023-03-03 |  PlayGames | Enterprise 64 & 128 - The Chessmaster 2000 | 0:31 | 8 |
| 2023-02-27 |  La Mazmorra Abandon | The Chessmaster 2000 (The Software Toolworks) (MS-DOS) [1986] [PC Longplay] | 14:04 | 220 |
| 2023-02-03 |  petsasjim1 | ATARI ST THE CHESSMASTER 2000 By The Software Toolworks & Electronic Arts In 1986 | 3:38 | 10 |
| 2023-01-12 | Ryan Baumann | Moof A Day: The Chessmaster 2000 v1.02 (Macintosh, 1986) | 12:49 | 25 |
| 2023-01-05 |  Renaldo Lo Muto | The Chessmaster 2000 (Atari ST / Gameplay) | 3:51 | 49 |
| 2023-01-05 | Renaldo Lo Muto | Chess Player 2150 (Atari ST / Gameplay) | 5:02 | 12 |
| 2022-08-12 | petsasjim1 | SINCLAIR ZX SPECTRUM Chess Master CHESSMASTER 1984 Serin Software Computer Tape Side A+B | 2:36 | 24 |
| 2022-06-24 |  UnknDoomer's corner of ultra silence | The Chessmaster 2000 (1986). Gameplay. For Old-Games.ru #87. | 15:24 | 9 |
| 2022-05-23 |  GET OFF MY LAWN | Random DOS Game Show #524: Chessmaster 2000 (1986) | 7:24 | 114 |
| 2022-04-25 | Ivan Paduano | Game of the day 3548 The Chessmaster 2000 Electronic Arts 1986 | 9:24 | 25 |
| 2022-01-28 | Nas_Sutromi | Zx Spectrum 128k Real Tape: ChessMaster 2000 | 12:52 | 6 |
| 2022-01-13 |  봉샘의 게임박물관 | [DOS 게임] 체스마스터 2000(1986) | 10:02 | 29 |
| 2021-12-21 | Jason Doucette | Chessmaster 2000 - First Play since childhood | 30:52 | 117 |
| 2021-11-07 | MrPetari | Chessmaster2000 MSTE | 0:47 | 23 |
| 2021-08-25 | Xadrez Brasil | Já jogou contra o Chessmaster 2000 dos anos 80? | 44:26 | 15,511 |
| 2021-03-24 |  Lipos Retro Schachcomputer | Mephisto Exclusiv V vs. Chessmaster 2000 | 38:38 | 60 |
| 2021-03-22 | Alex Harkonnen75 | My TOP Amiga Games : The first and best big Amiga games 1986 1987 | 9:12 | 1,427 |
| 2021-01-21 | The VideoGames Museum | The Chessmaster 2000 © 1986 Software Toolworks - PC DOS - Gameplay | 8:45 | 436 |
| 2020-12-21 | Sven Dännart | Chessmaster 2000 / Atari St Version | 3:00 | 270 |
| 2020-02-04 | zxspectrumgames4 | The Chessmaster 2000 (DOS) | 16:02 | 63 |
| 2019-07-30 | petsasjim1 | Chessmaster 2000, The 1986 mp4 HYPERSPIN DOS MICROSOFT EXODOS NOT MINE VIDEOS | 0:36 | 22 |
| 2019-07-17 | Ace1000ks1975 | Chessmaster 4000 | 8:12 | 1,449 |
| 2018-12-29 | DAVIRO el camionero gamer | Emulando...1 CHESSMASTER 2000 / AMSTRAD CPC / DAVIRO | 16:12 | 93 |
| 2018-12-16 | Retro Playthrus | Chessmaster 2000 - Atari ST [022] PlayThru | 15:15 | 992 |
| 2017-04-27 | FunCade 64 | Chessmaster 2000 ~ Amiga | 0:35 | 159 |
| 2015-04-25 | Squakenet | Chessmaster 2000 gameplay (PC Game, 1986) | 6:37 | 6,023 |
| 2014-07-01 | 1GO ShortPlay Retro Games | 1GO Short Play - Chessmaster 2000 (Amiga) | 3:35 | 1,550 |
| 2013-12-29 | Enrique G. Gálvez | Chessmaster 2000 (PC) | 2:02 | 761 |
| 2013-07-26 | zxspectrumgames4 | Chessmaster 2000 (ZX Spectrum) | 15:47 | 445 |
| 2013-07-09 | petsasjim1 | ATARI ST CHESSMASTER 2000 By The Software Toolworks From Automation Compact Disk Menu No 141 st zip | 3:38 | 1,138 |
