| Year | Award | Winner |
|---|---|---|
| 2020 | ||
| Best Themed MM | Planet Coaster by Toby | |
| Best Guest MM | Once More From The Top by Zero | |
| Best Depth for Min Rules MM | Trivial by Induction by elara | |
| Most Fun MM | Count the Sheep by ISamEI, Liar's Casino by Zero | |
| Best Themed DM | Do Androids Dream of Electric Deathmatches? by ISamEI/uriquack | |
| Best Strategy DM | Duorail by jkittykitkat | |
| Best Psychological DM | Secret Chess by Toby | |
| Best Optimization DM | Element by Non-original Game | |
| Best Misc DM | RoboChess Championships by elara | |
| Most Fun DM | Matchmaker by Toby | |
| 2021 | ||
| Best Themed MM | Magician's Market by TGXAndy | |
| Best Guest MM | Midas' Gambit by Spicyman33 | |
| Best Depth for Min Rules MM | Social Snake by pseudonam | |
| Most Fun MM | Social Snake by pseudonam | |
| Best Themed DM | Roundabout by Grunkle Squeaky | |
| Best Strategy DM | Catchup by Non-original Game | |
| Best Psychological DM | Hornswoggle by Non-original Game | |
| Best Observation DM | Flower Field by e_is_cool | |
| Best Optimization DM | Dragon's Rage by TGXAndy, Flower Field by e_is_cool | |
| Best Misc DM | WarioWare by e_is_cool | |
| Most Fun DM | Flower Field by e_is_cool, Hornswoggle by Non-original Game | |
| 2022 | ||
| Best Themed MM | Blob Party by XNimus | |
| Best Team MM | Paint You a Picture by Zero | |
| Best Guest MM | The Big Machine by chaotic_iak | |
| Best Depth for Min Rules MM | Pointing the Finger by Zero | |
| Most Fun MM | The Nonary Game by MarcerMercer | |
| Best Themed DM | Solitaire Chess by Zero | |
| Best Strategy DM | Sliding Tic-Tac-Toe by Myth, Solitaire Chess by Zero | |
| Best Psychological DM | Wizards' Duel by Deusovi | |
| Best Optimization DM | Quattro Loop by Zero | |
| Best Misc DM | Dicemons by Zero | |
| Most Fun DM | Blob Fighter by XNimus | |
| 2023 | ||
| Best Themed MM | Co-op QWOP by MathTurtle/Pumbledore | |
| Best Early Game MM | Dead First, Dead Last by RedsToad | |
| Best Mid Game MM | Advent of Language by e_is_cool/elara | |
| Best Late Game MM | Subliminal Message by ItzShaun | |
| Best Depth for Min Rules MM | Triforce Building by RedsToad | |
| Most Fun MM | Subliminal Message by ItzShaun | |
| Best Themed DM | Mages' Ballad by e_is_cool | |
| Best Strategy DM | Mages' Ballad by e_is_cool | |
| Best Psychological DM | The Eighteenth Hell by e_is_cool/elara | |
| Best Mental DM | Laser Lawn by MarcerMercer/RedsToad | |
| Best Misc DM | Absurdle by ItzShaun | |
| Best Depth for Min Rules DM | Toxicology by Techno Knight | |
| Most Fun DM | Absurdle by ItzShaun, Mages' Ballad by e_is_cool | |
| 2024 | ||
| Best Themed MM | Memories of a Lost Season by e_is_cool/elara | |
| Best Early Game MM | Swap 61 by pseudonam | |
| Best Mid Game MM | Hexagonal Highway by pseudonam | |
| Best Late Game MM | U-Boat Shootout by Isa/ISamEI | |
| Best Depth for Min Rules MM | Swap 61 by pseudonam | |
| Most Innovative MM | Memories of a Lost Season by e_is_cool/elara | |
| Most Fun MM | Memories of a Lost Season by e_is_cool/elara | |
| Best MM | Swap 61 by pseudonam | |
| Best Themed DM | Mitosis by pseudonam | |
| Best Strategy DM | Mitosis by pseudonam | |
| Best Psychological DM | Renounce Fate by Zero | |
| Best Mental DM | Logical Horror by e_is_cool/elara | |
| Best Misc DM | Boundary of Few and Many by pseudonam | |
| Best Depth for Min Rules DM | Mitosis by pseudonam | |
| Most Innovative DM | Gravity Pandemic by XNimus | |
| Most Fun DM | A Warrior's Death by e_is_cool/elara, Boundary of Few and Many by pseudonam | |
| Best DM | Mitosis by pseudonam |