| 1. |  Xadrez Brasil | Já jogou contra o Chessmaster 2000 dos anos 80? | 1,533 | |
| 2. |  Alex Harkonnen75 | My TOP Amiga Games : The first and best big Amiga games 1986 1987 | 37 | |
| 3. | Squakenet | Chessmaster 2000 gameplay (PC Game, 1986) | 30 | |
| 4. |  Thousand and One Adventure | Sfida a scacchi tra 8 bit / ZX Spectrum vs Commodore 64 | 26 | |
| 5. |  Ace1000ks1975 | Chessmaster 4000 | 17 | |
| 6. | La Mazmorra Abandon | The Chessmaster 2000 (The Software Toolworks) (MS-DOS) [1986] [PC Longplay] | 16 | |
| 7. |  GET OFF MY LAWN | Random DOS Game Show #524: Chessmaster 2000 (1986) | 13 | |
| 8. |  Sven Dännart | Chessmaster 2000 / Atari St Version | 9 | |
| 9. | DAVIRO el camionero gamer | Emulando...1 CHESSMASTER 2000 / AMSTRAD CPC / DAVIRO | 9 | |
| 10. | Lipos Retro Schachcomputer | Mephisto Exclusiv V vs. Chessmaster 2000 | 7 | |
| 11. | 1GO ShortPlay Retro Games | 1GO Short Play - Chessmaster 2000 (Amiga) | 6 | |
| 12. |  petsasjim1 | ATARI ST CHESSMASTER 2000 By The Software Toolworks From Automation Compact Disk Menu No 141 st zip | 5 | |
| 13. | zxspectrumgames4 | Chessmaster 2000 (ZX Spectrum) | 5 | |
| 14. | Enrique G. Gálvez | Chessmaster 2000 (PC) | 4 | |
| 15. | Jason Doucette | Chessmaster 2000 - First Play since childhood | 4 | |
| 16. |  Renaldo Lo Muto | The Chessmaster 2000 (Atari ST / Gameplay) | 4 | |
| 17. | petsasjim1 | SINCLAIR ZX SPECTRUM Chess Master CHESSMASTER 1984 Serin Software Computer Tape Side A+B | 3 | |
| 18. | FunCade 64 | Chessmaster 2000 ~ Amiga | 3 | |
| 19. | Ryan Baumann | Moof A Day: The Chessmaster 2000 v1.02 (Macintosh, 1986) | 2 | |
| 20. | Ivan Paduano | Game of the day 3548 The Chessmaster 2000 Electronic Arts 1986 | 2 | |
| 21. |  Robert's Retro-Gaming | Atari 8-Bit Game Play, Chessmaster 2000 | 2 | |
| 22. |  봉샘의 게임박물관 | [DOS 게임] 체스마스터 2000(1986) | 1 | |
| 23. | petsasjim1 | Chessmaster 2000, The 1986 mp4 HYPERSPIN DOS MICROSOFT EXODOS NOT MINE VIDEOS | 1 | |
| 24. | Nas_Sutromi | Zx Spectrum 128k Real Tape: ChessMaster 2000 | 1 | |
| 25. | MrPetari | Chessmaster2000 MSTE | 1 | |
| 26. | Renaldo Lo Muto | Chess Player 2150 (Atari ST / Gameplay) | 0 | |
| 27. | zxspectrumgames4 | The Chessmaster 2000 (DOS) | 0 | |
| 28. |  UnknDoomer's corner of ultra silence | The Chessmaster 2000 (1986). Gameplay. For Old-Games.ru #87. | 0 | |
| 29. | The VideoGames Museum | The Chessmaster 2000 © 1986 Software Toolworks - PC DOS - Gameplay | 0 | |
| 30. | SwiftSmash Gaming Zone | The Chessmaster 2000 Gameplay (SNES) | 0 | |
| 31. | Retro Playthrus | Chessmaster 2000 - Atari ST [022] PlayThru | 0 | |
| 32. | PlayGames | Enterprise 64 & 128 - The Chessmaster 2000 | 0 | |
| 33. | petsasjim1 | ATARI ST THE CHESSMASTER 2000 By The Software Toolworks & Electronic Arts In 1986 | 0 | |
