| 1. |  Jeremy Parish | Video Works | The Chessmaster retrospective: Every move's among the purest | Super NES Works #010 | 123 | |
| 2. | ZaffreRevolution | Every Inti Creates Game Ranked - ZaffreRevolution | 108 | |
| 3. | KarmaJolt | Multiple Consecutive Moves in The Chessmaster (Game Boy) - A Wild Glitch Appears! #shorts | 39 | |
| 4. | Good Old Days Gaming | The Chessmaster (NES) - Let's Play A Casual Game | 28 | Let's Play |
| 5. | NintendoComplete | The Chessmaster (NES) Playthrough | 23 | Let's Play |
| 6. | Hack Games Longplay Channel | Super Chess Master - Hack of The Chessmaster [GB] | 21 | |
| 7. | Kenshin1913 | Let's Play The Chessmaster (part 1) | 20 | Let's Play |
| 8. | LongplayArchive | Longplay of The Chessmaster | 18 | |
| 9. | Bad Game Hall of Fame | Bad Game Music: The Chessmaster (SNES) - "[Title Screen]" | 17 | |
| 10. | Nightcaps & Nostalgia | Don't drink and EBAY | The Chessmaster (NES) | 16 | |
| 11. | Niko's 8BitStereo | The Chessmaster (NES) Soundtrack - 8BitStereo | 15 | |
| 12. | Retro Comparisons | Game Boy Vs Game Gear - The Chessmaster | 14 | |
| 13. | Maxonum | Winner of the *FREE* ChessMaster for the PlayStation 2 | 13 | Guide |
| 14. | Maxonum | *FREE* ChessMaster for the PlayStation 2 | 12 | Guide |
| 15. | Ace1000ks1975 | The Chessmaster (1989) NES Soundtrack | 11 | |
| 16. | Vizzed Gameplay Videos | Chess-Master (GBC / Game Boy Color) - Vizzed.com GamePlay | 8 | |
| 17. | TheSBWproductions | SampleBW - The Chessmaster [SNES] (tournament level play) | 7 | |
| 18. | Kenshin1913 | Let's Play The Chessmaster (part 2) | 7 | |
| 19. | Retro Comparisons | NES Vs Game Boy Color - The Chessmaster | 6 | |
| 20. | Ogles Tutorials | The Queen's Gambit - The Official Video Game | 6 | |
| 21. | Jerry Young | The 133rd game a day game is The ChessMaster on the NES | 5 | |
| 22. | Real Strategy Gaming | Snes Chessmaster and 2005 Fritz vs Komodo25 | 5 | |
| 23. | Game Quest GB | The Chessmaster 1991 Game Boy | 4 | |
| 24. | Ephraim225 | Chess Vlog #6 feat. The Chessmaster (NES) | 4 | |
| 25. | 10 Minute Gamer | 10MG Plays The Chessmaster on NES | 4 | Let's Play |
| 26. | PennySaver | CHESSMASTER ON THE SNES (ft. My Brother) | 4 | |
| 27. | vertigo2hell | Becoming the Chessmaster || #shorts #harvester | 4 | |
| 28. | Kenshin1913 | Let's Play The Chessmaster (part 1.2) | 3 | |
| 29. | Brandon Evans | [HD] TAS: NES The Chessmaster (USA) in 00:07.12 by FractalFusion | 3 | |
| 30. | IcyRoserade | Kneel Before the Chessmaster | 2 | |
| 31. | SquallSnake | Chessmaster is another game to directly incorporate the falling Nintendo logo into gameplay | 2 | Vlog |
| 32. | davidb69 | Episode 7 retro gameplay from my n64 and snes collection- SNES the chessmaster game 3 of Feb VGM box | 2 | |
| 33. | Norrin Radd II Turbo | The Chessmaster NES | 2 | |
| 34. | Vicariously Retro | Chessmaster - NES Review | 2 | Review |
| 35. | RetroRobby | The ChessMaster (Game Gear) | 2 | |
| 36. | Krooked Does Stuff | Unscripted Episode 51: The Chessmaster (SNES) | 2 | Show |
| 37. | DeathlessNES | The Chessmaster 8 Second Checkmate - (DeathlessNES) | 2 | |
| 38. | randomaccount | The Chessmaster (SNES) Level 60/5 WR (16.922) | 1 | |
| 39. | nensondubois | The Chessmaster SNES Japanese Version Theme Full Version | 1 | |
| 40. | Jessica "The Coroner" Drapp | Rob's Random Roms: The Chessmaster | 1 | |
| 41. | Ace1000ks1975 | Chessmaster 4000 | 1 | |
| 42. | The Spazardous | NES Beats: Chessmaster | 1 | |
| 43. | desmaku | Let's Play The Chessmaster - Part 1 | 1 | Let's Play |
| 44. | Vizzed Gameplay Videos | The Chessmaster (NES / Nintendo) - Vizzed.com GamePlay | 1 | |
| 45. | Toad Speedgaming (Toad22484) | Chessmaster NES Blitz Game Audio Only | 1 | |
| 46. | randomaccount | The Chessmaster (NES) Newcomer 1 PB (8.819) | 1 | |
