| 1. | TheBreadghost | Chessmaster (Part 2) [GBA Journey #184] | 11:17:53 | |
| 2. | TheBreadghost | Chessmaster (Part 1) [GBA Journey #184] | 9:35:03 | |
| 3. |  Longplay Universe | Chessmaster (Part 2 of 2) - GBC Longplay/Walkthrough #106 [4Kp60] | 5:48:34 | Walkthrough |
| 4. |  HEAVENSARMY | Chessmaster: E5 (I'm Done The Tutorials On This Game) | 4:50:12 | |
| 5. | HEAVENSARMY | Chessmaster: E2 (DO NOT WATCH TO THE END) | 4:35:36 | |
| 6. | HEAVENSARMY | Chessmaster (My First Box Game Is Chess) | 4:17:49 | |
| 7. | TheBreadghost | Chessmaster (Part 3) [GBA Journey #184] | 3:11:54 | |
| 8. |  Retro Maniac | Let's Play "Chessmaster" (PS2) *Blind* - Part 1 | 1:28:27 | |
| 9. | JAVA Mobile Games / Ява Мобильные Игры | "Chessmaster" - Gameloft (Java Game) | 1:16:02 | |
| 10. | The Dragon Of Hatred | GameBoy Color Chaos - ChessMaster- (GBC Game #13) (Nintendo Game #27) | 1:04:32 | |
| 11. | CChesster | Chessmaster 11 - Tournament Tear - 38 | 49:20 | |
| 12. |  GAME • CHANNEL | Играем в Шахматишки на Play Blitz Chess Online - Пробуем новую ИГРОВУЮ ЗОНУ! | 36:33 | |
| 13. |  Iniciativa Xadrez | Análise - Rick (Chessmaster) vs Mathias (Man vs Machine - Jogo 1) | 31:57 | |
| 14. |  RetroDetect | Chessmaster PS2 Battlefield Gameplay (Ubisoft) | 29:57 | Let's Play |
| 15. | Lucky Yehohanan | Chessmaster (USA) - GBA (CPU Chessmaster lose while P1 wins) My Boy! emulator. | 29:22 | |
| 16. | The Silly Steve Show | Chessmaster - Part 3 - The Rematch . Bullet match , Let's play chess !! | 28:36 | |
| 17. | The Silly Steve Show | Chessmaster - Part 2 - Spoilers , i blunder in the endgame to a 1400 ?? Happy Gaming !! | 25:55 | |
| 18. | The Silly Steve Show | Chessmaster - Part 4 - Some bullet chess. i totally get crushed in the openings. i need practice !! | 25:55 | |
| 19. | Iniciativa Xadrez | Análise - Mathias vs Rick (Chessmaster) (Man vs Machine - Jogo 2) | 25:34 | |
| 20. | Fabio 5.56 | Chess [1] - Mateo | 24:54 | |
| 21. | Miller The Official Gaming | Chessmaster Gameplay Basic Tutorial and Standard Game GBA | 23:19 | Tutorial |
| 22. | SilasSama | Chess Break: Part 1: Chessmaster | 22:37 | |
| 23. | Nicolasxd 117 | ganandole a wendy de ps2 chessmaster | 20:56 | |
| 24. | Ace1000ks1975 | Chessmaster 4000 Turbo (1994) Soundtracks Roland MT-32 | 18:52 | |
| 25. | Andre Elpedes | Chessmaster (GBA) - “Classic Chess Set” | 18:48 | |
| 26. | Lucky Yehohanan | Chessmaster (USA) - GBA (opponent Ben lose while P1 wins) My Boy! emulator. | 17:36 | |
| 27. | CChesster | Chessmaster 11 - Inconsistent Difficulty - 73 | 16:20 | |
| 28. | Andre Elpedes | Chessmaster (GBA) - “Wood Chess Set” | 16:12 | |
| 29. | Tsurai Wataame | 10 Minute 1st Impressions : Chessmaster (PS2) | 14:41 | |
| 30. | Videoteca de jogos antigos | ChessMaster - Xbox Classic Gameplay | 14:36 | |
| 31. | Andre Elpedes | Chessmaster (GBA) - “Newspaper Chess Set” | 14:36 | |
| 32. |  Nightmare4k | Chessmaster 10th Edition Gameplay (Windows 8 compatible) | 13:37 | |
| 33. | Family Friendly Gaming | Chessmaster Part 1 | 13:07 | |
| 34. | Family Friendly Gaming | Chessmaster Part 2 | 12:38 | |
| 35. | The Silly Steve Show | Chessmaster - part 1 - Keep calm and push those pawns !! | 11:56 | |
| 36. | xboxbbcity | Chessmaster Xbox Gameplay | 11:47 | |
| 37. | Mac M78 : My Official Channel | Chessmaster ♟️ (GBC) - Test Gameplay | 11:10 | |
| 38. | CChesster | Chessmaster 11 - Deathfield Chess - 74 | 11:08 | |
| 39. | Wasted Youths | Master Sim Chess: Rated Game - Skippy [Rating 643] | 11:08 | |
| 40. | Andre Elpedes | Tani Adewumi vs. GothamChess/Levy Rozman [ROUND 1] in Chessmaster 10th Edition Style | 10:06 | |
| 41. | Wasted Youths | Master Sim Chess: Rated Game - Tex [Rating 427] | 10:01 | |
| 42. | 10min Gameplay | Chessmaster ... (PS2) Gameplay | 10:01 | |
| 43. | 10min Gameplay | Chessmaster ... (GBA) Gameplay | 10:01 | |
| 44. | Wasted Youths | Master Sim Chess: Rated Game - Manny [Rating 500] | 9:19 | |
| 45. | Andre Elpedes | Chessmaster (GBA) - “Dogs Chess Set” | 8:23 | |
| 46. | supersaiyancurt28 | ChessMaster On Ps2 | 8:23 | |
| 47. | Andre Elpedes | Chessmaster (GBA) - “Fanatsy Chess Set” | 8:03 | |
| 48. | Prehistoric Films | Let's Play Chessmaster | 7:57 | Let's Play |
| 49. | Squakenet | Chessmaster 2100 gameplay (PC Game, 1988) | 7:28 | |
| 50. | Andre Elpedes | Chessmaster (GBA) - “Circus Chess Set” | 7:14 | |
| 51. | Lucky Yehohanan | video Testing, Cropped one time. Chessmaster gba. | 6:40 | |
| 52. | TeslaOldgamesGameplay | Chessmaster 5500 gameplay | 6:31 | |
| 53. | Żabol | Chessmaster Gameplay [GBA] [No-Com] | 6:04 | |
| 54. |  The Video Game Museum | Game Boy Advance - Chessmaster © 2002 Ubisoft - Gameplay | 5:59 | |
| 55. | JustPlayGames | Chessmaster - ps2 | 5:57 | |
| 56. |  Denoobeur | Chessmaster/ Découverte GBA / FR/ Gameplay | 5:23 | |
| 57. |  Ireland Deity | CHESS Aaron vs Chessmaster Nintendo DSi XL 1-0 15:00 Minute Unrated Game 14.05.16 | 5:20 | |
| 58. |  Retro Content Weekly | Chessmaster retrospective (1986-1996) | 5:14 | |
| 59. | Andre Elpedes | Bill Gates vs. Magnus Carlsen in Chessmaster 10th Edition Style [PC] | 4:55 | |
| 60. |  Bharathi AI | Protect your KING 👑 from Opponent in chess Game 🎮 #chessbaseindia #chesscom #chessmaster #chessgames | 4:44 | |
| 61. | Andre Elpedes | Chessmaster (GBA) - “Napoleon Chess Set” | 4:34 | |
| 62. | Blue Light Fox | Chessmaster (PS2) - Gameplay on PCSX2 | 4:23 | |
| 63. | Zack “SquallSnake” G | GBA Single-Pak Link - ChessMaster (lots of options and visual themes for a classic game) | 4:03 | |
| 64. |  Ben Sutarno&kitty cat | Chessmaster ps2 | 3:33 | |
| 65. |  Benchmarks PRO | Master level chess play lost no 1 | 3:07 | |
| 66. | Waffles34 | Ryan vs Monkey Stanley Ranked Match | 2:55 | |
| 67. | JustPlayGames | Chessmaster - Nintendo Game Boy | 2:36 | |
| 68. | TheMadWasp Dumping Grounds | Chessmaster 10: Find Check, Queen, Rook, Bishop and Knight PBs | 2:32 | |
| 69. | Bharathi AI | Chess Brilliant #chessgame #chessmaster #chessplayer #chess #chessboard #chesscom #chessvideoplus | 2:20 | |
| 70. | Bharathi AI | @Chess Brilliant #chessgame #chessmaster #chessplayer #chess #chessboard #chesscom #chessvideoplus | 2:04 | |
| 71. | drg7 | chess|chess game|chess video|#chess #chessgame #chesscom #chessvideoplus #chesstricks #chessmaster | 1:58 | |
| 72. | Bharathi AI | @Chess Brilliant #chessgame #chessmaster #chessplayer #chess #chessboard #chesscom #chessvideoplus | 1:46 | |
| 73. | drg7 | chess game|chess|chess master|checkmate|#chess #chessgame #chesscom #chessvideoplus #chessmaster | 1:44 | |
| 74. | drg7 | chess tricks|chess game🎯|chess video|#chess #chessgame #chesscom#chessmaster #tricks #chessbaseindia | 1:37 | |
| 75. | Bharathi AI | Excellent Grandmaster Game @Grandmaster_Bharathi #chessgame #chessmaster #chessplayer #chessvideoplus | 1:33 | |
| 76. | drg7 | chess tricks|chess game|chess video|#chess #chessbaseindia #chessgame #chesstricks #chessmaster | 1:33 | |
| 77. | Bharathi AI | Other Draw types #chessbrilliant #chesscom #chessgame #chessdraw #chess #chesslover #chessmaster | 1:03 | |
| 78. | Jokowae | amazing game🌟🌟🌟 #chessmaster #chess #short ches | 0:51 | |
| 79. |  Patriciooo | Chessmaster more like more like chess disaster | 0:50 | |
| 80. | Now Loading Please Wait | Chessmaster - Xbox | 0:40 | |
| 81. | Mondity | 0 elo funny chess tactics #chess #chessgame #chesstactics #chesscom #chessmaster #chessvideoplus #ch | 0:39 | |
| 82. | Now Loading Please Wait | Chessmaster USA - Game Boy Advance (GBA) | 0:38 | |
| 83. | Bharathi AI | I Have Been Submitted The Brilliant Move By bharathi #chess #chessgames #chessbrilliant #chessmaster | 0:38 | |
| 84. |  Arcade Forever | GBA ► Chessmaster | 0:37 | |
| 85. | Encyclopegames | Game Boy Advance Chessmaster | 0:37 | |
| 86. | hyperspinbrasil | Chessmaster USA - Game Boy Advance | 0:37 | |
| 87. | Arcade Forever | Nintendo Game Boy ► GB ► Chessmaster, The | 0:36 | |
| 88. | Arcade Forever | Sony PS2 ► Chessmaster | 0:36 | |
| 89. | IGN | Chessmaster PlayStation 2 Gameplay_2003_06_03 | 0:31 | Let's Play |
| 90. | PidgiWiki | Game Boy Advance Chessmaster 20020322 | 0:31 | |
| 91. | Bharathi AI | Brilliancy game @Grandmaster_Bharathi #chessgame #chessmaster #chessboard #chesscom #chessvideoplus | 0:31 | |
| 92. | Bharathi AI | Other Draw types in chess#chessbrilliant #chessmaster #chesscom #chesslover #chess #chessgame | 0:29 | |
| 93. |  My KingKulitan | #chess #chessmaster kapatid mong chessmaster | 0:19 | |
| 94. | Chess. is Otakurist | The price of greed | Chess | #chess #chessedit #chessmaster #game #chessgame #memes #trending #tren | 0:16 | |
