| 2024-11-02 |  FM TriniCupid | Chessmaster resigns in 9 Moves 😮 #chess #chessanalysis | 0:00 | 513 |
| 2024-01-30 | Mondity | 0 elo funny chess tactics #chess #chessgame #chesstactics #chesscom #chessmaster #chessvideoplus #ch | 0:39 | 2,416 |
| 2023-06-03 | The Dragon Of Hatred | GameBoy Color Chaos - ChessMaster- (GBC Game #13) (Nintendo Game #27) | 1:04:32 | 3 |
| 2023-04-13 | Miller The Official Gaming | Chessmaster Gameplay Basic Tutorial and Standard Game GBA | 23:19 | 51 |
| 2022-02-08 | Zack “SquallSnake” G | GBA Single-Pak Link - ChessMaster (lots of options and visual themes for a classic game) | 4:03 | 408 |
| 2022-01-28 | supersaiyancurt28 | ChessMaster On Ps2 | 8:23 | 150 |
| 2020-07-25 | Ace1000ks1975 | Chessmaster 4000 Turbo (1994) Soundtracks Roland MT-32 | 18:52 | 448 |
| 2019-12-21 | HEAVENSARMY | Chessmaster: E5 (I'm Done The Tutorials On This Game) | 4:50:12 | 4 |
| 2019-12-18 | HEAVENSARMY | Chessmaster: E2 (DO NOT WATCH TO THE END) | 4:35:36 | 3 |
| 2019-12-17 | HEAVENSARMY | Chessmaster (My First Box Game Is Chess) | 4:17:49 | 13 |
| 2019-08-06 | Fabio 5.56 | Chess [1] - Mateo | 24:54 | 11 |
| 2018-10-21 | JAVA Mobile Games / Ява Мобильные Игры | "Chessmaster" - Gameloft (Java Game) | 1:16:02 | 945 |
| 2015-09-27 | CChesster | Chessmaster 11 - Deathfield Chess - 74 | 11:08 | 8 |
| 2015-09-20 | CChesster | Chessmaster 11 - Inconsistent Difficulty - 73 | 16:20 | 45 |
| 2015-04-27 | Family Friendly Gaming | Chessmaster Part 2 | 12:38 | 46 |
| 2015-04-27 | Family Friendly Gaming | Chessmaster Part 1 | 13:07 | 192 |
| 2015-01-19 | CChesster | Chessmaster 11 - Tournament Tear - 38 | 49:20 | 143 |
| 2014-12-17 | Prehistoric Films | Let's Play Chessmaster | 7:57 | 43 |
| 2013-11-14 | Encyclopegames | Game Boy Advance Chessmaster | 0:37 | 400 |
| 2011-05-19 | IGN | Chessmaster PlayStation 2 Gameplay_2003_06_03 | 0:31 | 1,000 |
