| 1. |  Xadrez Brasil | 15,511 | Já jogou contra o Chessmaster 2000 dos anos 80? | 44:26 |
| 2. | Squakenet | 6,023 | Chessmaster 2000 gameplay (PC Game, 1986) | 6:37 |
| 3. |  1GO ShortPlay Retro Games | 1,550 | 1GO Short Play - Chessmaster 2000 (Amiga) | 3:35 |
| 4. |  Ace1000ks1975 | 1,449 | Chessmaster 4000 | 8:12 |
| 5. |  Alex Harkonnen75 | 1,427 | My TOP Amiga Games : The first and best big Amiga games 1986 1987 | 9:12 |
| 6. |  petsasjim1 | 1,194 | ATARI ST THE CHESSMASTER 2000 By The Software Toolworks & Electronic Arts In 1986 | 3:38 |
| 7. | Retro Playthrus | 992 | Chessmaster 2000 - Atari ST [022] PlayThru | 15:15 |
| 8. | Enrique G. Gálvez | 761 | Chessmaster 2000 (PC) | 2:02 |
| 9. | zxspectrumgames4 | 508 | The Chessmaster 2000 (DOS) | 16:02 |
| 10. |  The VideoGames Museum | 436 | The Chessmaster 2000 © 1986 Software Toolworks - PC DOS - Gameplay | 8:45 |
| 11. |  Sven Dännart | 270 | Chessmaster 2000 / Atari St Version | 3:00 |
| 12. | Thousand and One Adventure | 238 | Sfida a scacchi tra 8 bit / ZX Spectrum vs Commodore 64 | 14:13 |
| 13. | La Mazmorra Abandon | 220 | The Chessmaster 2000 (The Software Toolworks) (MS-DOS) [1986] [PC Longplay] | 14:04 |
| 14. | Jason Doucette | 117 | Chessmaster 2000 - First Play since childhood | 30:52 |
| 15. | GET OFF MY LAWN | 114 | Random DOS Game Show #524: Chessmaster 2000 (1986) | 7:24 |
| 16. | DAVIRO el camionero gamer | 93 | Emulando...1 CHESSMASTER 2000 / AMSTRAD CPC / DAVIRO | 16:12 |
| 17. |  Renaldo Lo Muto | 61 | The Chessmaster 2000 (Atari ST / Gameplay) | 3:51 |
| 18. | Lipos Retro Schachcomputer | 60 | Mephisto Exclusiv V vs. Chessmaster 2000 | 38:38 |
| 19. |  봉샘의 게임박물관 | 29 | [DOS 게임] 체스마스터 2000(1986) | 10:02 |
| 20. | Ryan Baumann | 25 | Moof A Day: The Chessmaster 2000 v1.02 (Macintosh, 1986) | 12:49 |
| 21. | Ivan Paduano | 25 | Game of the day 3548 The Chessmaster 2000 Electronic Arts 1986 | 9:24 |
| 22. | MrPetari | 23 | Chessmaster2000 MSTE | 0:47 |
| 23. | SwiftSmash Gaming Zone | 17 | The Chessmaster 2000 Gameplay (SNES) | 10:15 |
| 24. |  Robert's Retro-Gaming | 9 | Atari 8-Bit Game Play, Chessmaster 2000 | 21:37 |
| 25. |  UnknDoomer's corner of ultra silence | 9 | The Chessmaster 2000 (1986). Gameplay. For Old-Games.ru #87. | 15:24 |
| 26. | PlayGames | 8 | Enterprise 64 & 128 - The Chessmaster 2000 | 0:31 |
| 27. | Nas_Sutromi | 6 | Zx Spectrum 128k Real Tape: ChessMaster 2000 | 12:52 |
