| 1. |  TikTak Draw | THE CHESSMASTER | Draw My Life | Creepypasta | 148,513 | |
| 2. | Draw The Life TikTak | THE CHESSMASTER | Draw My Life | 16,668 | |
| 3. | slobulus | CHESSMASTER (SNES) - Machacando a la Super Nintendo en el tablero || Gameplay / Morralla Clásica | 1,527 | |
| 4. |  QuakedoomNukem | Rayman Redemption - All Bosses (Normal) | 1,118 | |
| 5. |  HumMy - CHUYỆN KỂ KINH DỊ 3S | Cơn thịnh nộ của The Chessmaster đáng sợ phá Đạo lý| Creepypasta thần Cờ vua bị lãng quên #shorts | 1,061 | |
| 6. |  KarmaJolt | Multiple Consecutive Moves in The Chessmaster (Game Boy) - A Wild Glitch Appears! #shorts | 843 | |
| 7. | Jeremy Parish | Video Works | The Chessmaster retrospective: Every move's among the purest | Super NES Works #010 | 755 | |
| 8. | ZaffreRevolution | Every Inti Creates Game Ranked - ZaffreRevolution | 637 | |
| 9. |  LetsPlayOldGames | The Chessmaster on SNES | 225 | |
| 10. | TASVideosChannel | [TAS] NES The Chessmaster by FractalFusion in 00:06.75 | 209 | |
| 11. | KYLXBN (Kyle) | Bullying a NES chess game with the world's strongest chess engine | 197 | |
| 12. | NintendoComplete | The Chessmaster (NES) Playthrough | 186 | Let's Play |
| 13. | World of Longplays | SNES Longplay [664] The Chessmaster (US) | 169 | |
| 14. |  Totally Pointless Youtube Channel | The Chessmaster gameplay (SNES) | 164 | |
| 15. | Good Old Days Gaming | The Chessmaster (NES) - Let's Play A Casual Game | 147 | Let's Play |
| 16. |  Kikoskia | Let's Play The Chessmaster | 141 | Let's Play |
| 17. |  The Mexican Runner | 454/714 The Chessmaster - NESMania | 136 | Let's Play |
| 18. | Charles Atencio | PBS NOVA - The Chip vs. The Chessmaster (1991) | 124 | |
| 19. | World of Longplays | Game Boy Advance Longplay [386] Chessmaster (US) | 123 | |
| 20. | Hack Games Longplay Channel | Super Chess Master - Hack of The Chessmaster [GB] | 116 | |
| 21. | MrThiagoBoni | Zerando The Chessmaster (SNES) em 06 minutos - Level of Play Is 2 [TAS] | 94 | |
| 22. | LongplayArchive | Longplay of The Chessmaster | 88 | |
| 23. | SaturnTAS | Chessmaster (SNES) - Quickest Checkmate on hardest difficulty | 86 | |
| 24. | AqualungGameReviews | Chessmaster NES Review | 70 | Review |
| 25. |  Nestalgica | The Chessmaster (NES) [METAL COVER] | 62 | |
| 26. | Niko's 8BitStereo | The Chessmaster (NES) Soundtrack - 8BitStereo | 50 | |
| 27. | Bad Game Hall of Fame | Bad Game Music: The Chessmaster (SNES) - "[Title Screen]" | 49 | |
| 28. |  Gameboy Challenger | The Chessmaster (1991 Hi Tech Expressions) [All the Game Boy Shorts] | 39 | |
| 29. | VGdrum | VGdrum - The Chessmaster | 32 | |
| 30. | 10min Gameplay | The Chessmaster ... (SNES) 60fps Gameplay | 29 | |
| 31. |  Yonic87 | Le Full Set mondial Sega Game Gear #33 | 21 | |
| 32. | JBD | Analogue Pocket - The Chessmaster - FPGA : Game Gear | 20 | |
| 33. |  Torne | The Chessmaster Walkthrough | 19 | Walkthrough |
| 34. |  Retro Gaming Junction | Chessmaster Review | SNES Chronicles Ep 9 | September 1, 1991 | 19 | Review |
| 35. | Barbie Chêtif | Review de merde #1328 : The Chessmaster [Game Boy] | 18 | |
| 36. | SEGADriven.com | All Chess Games for SEGA Consoles | SEGADriven | 17 | |
| 37. | Ace1000ks1975 | The Chessmaster (1989) NES Soundtrack | 17 | |
| 38. | Vizzed Gameplay Videos | Chess-Master (GBC / Game Boy Color) - Vizzed.com GamePlay | 16 | |
| 39. |  Flygon | NES The Chessmaster in 00:07.12 by FractalFusion | 15 | |
| 40. | Retro Comparisons | Chessmaster - NES Vs SNES | 15 | |
| 41. | Retro Comparisons | Game Boy Vs Game Gear - The Chessmaster | 15 | |
| 42. | Brandon Evans | [HD] TAS: NES The Chessmaster (USA) in 00:07.12 by FractalFusion | 15 | |
| 43. |  Gameplays and Longplays xD | The Chessmaster [SNES] GAMEPLAY | 14 | |
| 44. | sausage948 | The Chessmaster TAS 0:07 | 14 | |
| 45. | Real Strategy Gaming | Snes Chessmaster and 2005 Fritz vs Komodo25 | 14 | |
| 46. | Ogles | The Queen's Gambit - The Official Video Game | 13 | |
| 47. | Con Z al final | The Chessmaster - #NESiclopedia 117 | 14 | |
| 48. | E The Jumper | Rayman Redemption: The Chessmaster | 11 | |
| 49. | nensondubois | The Chessmaster SNES Japanese Version Theme Full Version | 11 | |
| 50. | Bombchu | Super Sunday - Episode 6: The Chessmaster | SNES 1991 | 10 | |
| 51. |  GPWT | The Chessmaster (NES - Dendy - Famicom - 8 bit) - Шахматы на денди на высокой сложности Walkthrough | 10 | Walkthrough |
| 52. | Lipos Retro Schachcomputer | SciSys Companion III vs. The Chessmaster SNES | 10 | |
| 53. | SNESStarApps | The Chessmaster Intro (SNES Introduction) | 9 | |
| 54. | Egon Spengler - Classic Games | [NES] THE CHESSMASTER - Part 1 | 9 | |
| 55. |  Shinespark | War Of The Warriors Runde 11: The Chessmaster Teil 2 /? | 9 | |
| 56. | OS GAMES10 | Chessmaster - EU JOGO #188 | 8 | |
| 57. | Johndo TV | JohnDo direct : SuperChess Master, le patch de The Chessmaster GB ♟️👑 | 8 | |
| 58. | Lipos Retro Schachcomputer | The Chessmaster SNES | 8 | |
| 59. | Classic Game Sessions | Chessmaster (NES) - full play through of this popular chess game for the NES! | 8 | Let's Play |
| 60. | Qenelcontinuo | The Chessmaster #emulador #batocera #recalbox #retro #gamer #gamegear #sega #jugadores #lowcost #pc | 8 | |
| 61. | spikevegeta | SNESMania Game 006: The Chessmaster | 9 | |
| 62. | Izumi kajiura | Chessmaster (NES) Speedrun in 8.730 | 8 | |
| 63. | UnknownD | Dee's NES Collection - 06: The Chessmaster | 7 | |
| 64. | Morgan Kell | The Chessmaster (Game Gear 60Hz) - Startup / Full Game AI vs. AI (Level 6, Deep Thinking ON) | 7 | |
| 65. | Ретро ТВ телепередачи и ШОУ про видеоигры и ПК игры | Let's Play BONUS - Мир Денди - The Chessmaster (Dendy) cut 001 | 7 | Let's Play |
| 66. | RetroRobby | The ChessMaster (Game Gear) | 7 | |
| 67. | Nightcaps & Nostalgia | Don't drink and EBAY | The Chessmaster (NES) | 7 | |
| 68. | GandalfJugon | Sega Chess | 7 | |
| 69. | World of RetroGaming | The worst Chess Game ever - Chessmaster for Sega Game Gear | 7 | |
| 70. | Kenshin1913 | Let's Play The Chessmaster (part 1) | 7 | Let's Play |
| 71. | Vicariously Retro | Chessmaster - NES Review | 6 | Review |
| 72. | Egon Spengler - Classic Games | [NES] THE CHESSMASTER - Part 2 | 6 | |
| 73. |  Perfeito Game | The ChessMaster - Um velho amigo | 6 | |
| 74. | Zack G | Chessmaster is another game to directly incorporate the falling Nintendo logo into gameplay | 9 | Vlog |
| 75. | Jugador Retro | Nos echamos un ajedrez?? The Chessmaster para Super Nintendo #jugadorretro #chess #ajedrez | 6 | |
| 76. | GandalfJugon | The Chessmaster (Game Gear) | 6 | |
| 77. | SMS Power! VGMs | The Chessmaster - Sega Game Gear - Craig B. Seastrom | 6 | |
| 78. | Felipe Nascimento | The Chessmaster (Game Gear) Newcomer Match | 6 | |
| 79. | Portable Power Podcast - Complete Game Boy Library | THE BEARDYMAN'S GAMBIT - The Chessmaster - Game Boy Review 157 | 6 | Review |
| 80. | Shinespark | War Of The Warriors Runde 11: The Chessmaster Teil 12 /?? | 6 | |
| 81. | Shinespark | War Of The Warriors Runde 11: The Chessmaster Teil 1 /? | 6 | |
| 82. | Daryl Allen | The Chessmaster (SNES) vs Stockfish12 (Lenovo T450) | 5 | |
| 83. | 88 Games por Hora - Rodrigo Guru | Desafio de Zeramento #24 - The Chessmaster (NES) - direto do console | 5 | |
| 84. |  DolmaKalem | [GBC] Chessmaster (1999) Longplay | 5 | Walkthrough |
| 85. | Norrin Radd II Turbo | The Chessmaster NES | 5 | |
| 86. | GamerJGB | Rayman Redemption: Playtopia (The Lair of the Chessmaster) [1080 HD] | 5 | |
| 87. | Révo SEGA 8-bit | Chessmaster v1 SEGA Master System GG2SMS Hack | 5 | |
| 88. | Gameboy Challenger | [GameBoy full game walkthrough] The Chessmaster (1991 Hi Tech Expressions) FHD 60fps | 5 | Walkthrough |
| 89. | Felipe Nascimento | The Chessmaster (Nes) Newcomer Match | 5 | |
| 90. |  Mr DotoroBear | jugamos Chessmaster en nes por Retrogames | 5 | |
| 91. | kardboardking | NES Chessmaster-- Human game | 5 | |
| 92. | Felipe Nascimento | The Chessmaster (Game Boy) Newcomer match | 5 | |
| 93. | FractalFusion | [TAS] The Chessmaster in 6.75 seconds | 5 | |
| 94. | Shinespark | War Of The Warriors Runde 11: The Chessmaster Teil 4 /? | 5 | |
| 95. | MrNorbert1994 | Chessmaster (NES) Playthrough -Normal Level- | 4 | |
| 96. | WorldOfSuperNintendo | The Chessmaster ESP Commercial Snes | 4 | |
| 97. | TheSBWproductions | SampleBW - The Chessmaster [SNES] (tournament level play) | 4 | |
| 98. | GingerSwitch | Wisdom From the Chessmaster | 4 | |
| 99. | Shinespark | War Of The Warriors Runde 11: The Chessmaster Teil 6 /? | 4 | |
| 100. | RetroStadium | Chessmaster (NES) - RetroStadium Ep.105 | 4 | |
