| 1. |  petsasjim1 | 4 | ATARI ST THE CHESSMASTER 2000 By The Software Toolworks & Electronic Arts In 1986 | 3:38 |
| 2. |  Renaldo Lo Muto | 2 | The Chessmaster 2000 (Atari ST / Gameplay) | 3:51 |
| 3. |  zxspectrumgames4 | 2 | The Chessmaster 2000 (DOS) | 16:02 |
| 4. |  SwiftSmash Gaming Zone | 1 | The Chessmaster 2000 Gameplay (SNES) | 10:15 |
| 5. |  봉샘의 게임박물관 | 1 | [DOS 게임] 체스마스터 2000(1986) | 10:02 |
| 6. |  Alex Harkonnen75 | 1 | My TOP Amiga Games : The first and best big Amiga games 1986 1987 | 9:12 |
| 7. |  PlayGames | 1 | Enterprise 64 & 128 - The Chessmaster 2000 | 0:31 |
| 8. | Ryan Baumann | 1 | Moof A Day: The Chessmaster 2000 v1.02 (Macintosh, 1986) | 12:49 |
| 9. |  Robert's Retro-Gaming | 1 | Atari 8-Bit Game Play, Chessmaster 2000 | 21:37 |
| 10. | MrPetari | 1 | Chessmaster2000 MSTE | 0:47 |
| 11. | DAVIRO el camionero gamer | 1 | Emulando...1 CHESSMASTER 2000 / AMSTRAD CPC / DAVIRO | 16:12 |
| 12. |  Sven Dännart | 1 | Chessmaster 2000 / Atari St Version | 3:00 |
| 13. | Nas_Sutromi | 1 | Zx Spectrum 128k Real Tape: ChessMaster 2000 | 12:52 |
| 14. |  Ivan Paduano | 1 | Game of the day 3548 The Chessmaster 2000 Electronic Arts 1986 | 9:24 |
| 15. | Retro Playthrus | 1 | Chessmaster 2000 - Atari ST [022] PlayThru | 15:15 |
| 16. |  UnknDoomer's corner of ultra silence | 1 | The Chessmaster 2000 (1986). Gameplay. For Old-Games.ru #87. | 15:24 |
| 17. | 1GO ShortPlay Retro Games | 1 | 1GO Short Play - Chessmaster 2000 (Amiga) | 3:35 |
| 18. | Jason Doucette | 1 | Chessmaster 2000 - First Play since childhood | 30:52 |
| 19. | Xadrez Brasil | 1 | Já jogou contra o Chessmaster 2000 dos anos 80? | 44:26 |
| 20. | Lipos Retro Schachcomputer | 1 | Mephisto Exclusiv V vs. Chessmaster 2000 | 38:38 |
| 21. | GET OFF MY LAWN | 1 | Random DOS Game Show #524: Chessmaster 2000 (1986) | 7:24 |
| 22. | The VideoGames Museum | 1 | The Chessmaster 2000 © 1986 Software Toolworks - PC DOS - Gameplay | 8:45 |
| 23. | La Mazmorra Abandon | 1 | The Chessmaster 2000 (The Software Toolworks) (MS-DOS) [1986] [PC Longplay] | 14:04 |
| 24. | Ace1000ks1975 | 1 | Chessmaster 4000 | 8:12 |
| 25. | Enrique G. Gálvez | 1 | Chessmaster 2000 (PC) | 2:02 |
| 26. | Thousand and One Adventure | 1 | Sfida a scacchi tra 8 bit / ZX Spectrum vs Commodore 64 | 14:13 |
| 27. | Squakenet | 1 | Chessmaster 2000 gameplay (PC Game, 1986) | 6:37 |
