| 1. |  xBuster6 | Chessmaster: The Art of Learning [Nintendo DS] Gameplay | 14 | |
| 2. |  Ajedrez White Bishop | Chessmaster Vs Eliud | 13 | |
| 3. |  SCORPION | Chessmaster Grandmaster Edition #8 часть | 11 | |
| 4. | 10min Gameplay | Chessmaster: The Art of Learning ... (PSP) Gameplay | 9 | |
| 5. | Владимир Голубев (volgame) | (PSP) Chessmaster The Art Of Learning (ULES-01013) GamePlay | 5 | |
| 6. | SCORPION | Chessmaster Grandmaster Edition #5 часть | 5 | |
| 7. | SCORPION | Chessmaster Grandmaster Edition #4 часть | 4 | |
| 8. |  mad4games65 | Chessmaster - The Art of Learning - Playstation Portable | 3 | |
| 9. | #Ziggyboishorts | Chessmaster PSP Gameplay HD | 3 | |
| 10. | SCORPION | Chessmaster Grandmaster Edition #9 часть | 2 | |
| 11. |  Playthrough Emporium | Chessmaster: The Art of Learning - HD PSP Gameplay - PPSSPP | 2 | |
| 12. |  Arcade Forever | Nintendo DS ► Chessmaster ► The Art of Learning | 2 | |
| 13. | SCORPION | Chessmaster Grandmaster Edition #7 часть | 2 | |
| 14. |  Ireland Deity | CHESS Chessmaster Nintendo DSi XL vs Aaron 0.5-0.5 50:00 Minute Unrated Game 12.05.16 | 2 | |
| 15. | GeorgeAtento | Game against Chessmaster Grandmaster X Personality (Laura 2138) | 1 | |
| 16. |  Matthew Doucette (Xonatron) | Chessmaster Grandmaster Edition (PC) - Xonatron vs. ''Amo 1496'' (0-1; lost on time) | 1 | |
| 17. |  KK Nintendo DS Game | Chessmaster: The Art of Learning (US) | 1 | |
| 18. | Игровой Стример | Chessmaster: The Art of Learning PPSSPP v.1.0.1 on Nvidia Shield Tablet (Android) | 1 | |
| 19. |  Now Loading Please Wait | Chessmaster The Art of Learning USA - Nintendo DS - Play in your Xbox One or Series! | 1 | |
| 20. |  ЯKAPUT | Chessmaster: The Art of Learning (Intro + Credits + Quick Game - Nintendo DS - Joshua Waitzkin) | 1 | |
| 21. | Matthew Doucette (Xonatron) | Chessmaster Grandmaster Edition (PC) - Xonatron vs. "Hayden 1294" (1-0) - First 40m of Gameplay | 1 | |
| 22. | SCORPION | Chessmaster Grandmaster Edition #6 часть | 1 | |
