The majority of awards are awarded at midnight, but some of them like hourly game winners are awarded instantly when that game ends. So if you break a major point barrier, check back the next day for your new award! We do not post Experienced and Veteran winners on this list. List Updated every 30 Minutes.
| Time | Player | Team | Award |
| Dec 08, 9:35 PM | Datsmeharse | Pi in the Sky | Winningest |
| Dec 04, 9:35 PM | Flukey | The Meek Shall Inherit | Winningest |
| Dec 02, 9:35 PM | SimonySeller | The Cat People | Winningest |
| Nov 17, 9:35 PM | lachicadecafe | Playing for fun | Winningest |
| Nov 12, 9:35 PM | mrfitz | --- | Winningest |
| Nov 10, 9:35 PM | pagea | Pi in the Sky | Winningest |
| Nov 10, 3:35 PM | LadyM5 | --- | Winningest |
| Oct 23, 9:35 AM | glenjue | DC Team | Winningest |
| Oct 18, 9:35 PM | vinton1640 | Triviabiz | Winningest |
| Oct 18, 9:35 AM | Bonniewest | --- | Winningest |
| Oct 12, 3:35 AM | MarchHare007 | Wisdom of the Fool | Winningest |
| Sep 28, 3:35 PM | teachdpo | Playing for fun | Winningest |
| Sep 27, 3:35 PM | GBfan | The Calculators | Winningest |
| Sep 25, 3:36 PM | Pudman | The Moops | Winningest |
| Sep 10, 3:35 PM | MissCirrus | Writer's Block | Winningest |
| Sep 09, 3:35 AM | zacd | --- | Winningest |
| Sep 05, 3:35 AM | MAAsv477 | LIGHTHEARTED RETURN | Winningest |
| Sep 02, 9:35 AM | wbarney | The Joli Llamas | Winningest |
| Sep 02, 3:34 AM | mungojerry | Dreamers | Winningest |
| Aug 27, 9:34 AM | Bowler413 | The Moops | Winningest |
| Aug 08, 9:34 AM | verbatimsa | The Calculators | Winningest |
| Jul 28, 9:35 PM | Yowser | --- | Winningest |
| Jul 28, 3:35 PM | alaspooryoric | The Regal Beagles | Winningest |
| Jul 24, 3:35 PM | pennie1478 | The Devil's Advocates | Winningest |
| Jul 23, 3:35 AM | Kalibre | Funsters | Winningest |
| Jul 22, 9:34 AM | jetskichimp | Vixens | Winningest |
| Jul 19, 3:35 PM | violet71 | The British | Winningest |
| Jun 17, 3:34 PM | rustic_les | The Calculators | Winningest |
| Jun 08, 3:34 PM | Kenners158 | Triviabiz | Winningest |
| Jun 07, 9:34 PM | matho_77 | The Regal Beagles | Winningest |
| Jun 06, 9:34 PM | bruins1956 | --- | Winningest |
| Jun 05, 3:34 PM | Steelflower75 | The Cat People | Winningest |
| May 30, 9:34 PM | lkluck | The Moops | Winningest |
| May 26, 3:34 PM | Smudge111 | Quizaholics Synonymous | Winningest |
| May 24, 9:34 PM | amyclutchpurse | Movie Buffs | Winningest |
| May 22, 3:34 PM | slay01 | The Bee's Knees | Winningest |
| May 21, 9:34 PM | clong14 | The Palmetto Players | Winningest |
| May 16, 9:34 PM | NumanKiwi | The Homo Sapiens | Winningest |
| May 16, 3:34 PM | 21okie | The Cat People | Winningest |
| May 16, 3:34 PM | gemellus | --- | Winningest |
| May 09, 9:34 PM | Asaint1949 | --- | Winningest |
| May 08, 9:34 AM | sonicblast | Friends of Jesus | Winningest |
| May 05, 9:34 PM | Lenny15 | Old Farts | Winningest |
| Apr 15, 9:34 PM | fgrozalen | The Devil's Advocates | Winningest |
| Apr 14, 3:34 PM | Emma058 | Red Hot Silly Beggars | Winningest |
| Apr 14, 3:34 AM | fletch1165 | The Meek Shall Inherit | Winningest |
| Apr 14, 3:34 AM | lones78 | The Joli Llamas | Winningest |
| Apr 12, 9:34 PM | Qmel | Dream Weavers | Winningest |
| Apr 08, 3:34 AM | mikiel | Writer's Block | Winningest |
| Apr 05, 9:34 PM | Taltarzac | The Calculators | Winningest |
| Mar 31, 9:34 PM | mensa58 | classicalmusic/mensan | Winningest |
| Mar 28, 3:34 AM | looegie | The Beeronians | Winningest |
| Mar 22, 9:34 PM | inkwell | Canadian Players | Winningest |
| Mar 21, 3:34 AM | sadwings | Kilted Kangas | Winningest |
| Mar 20, 9:34 PM | LancYorkYank | Red Hot Silly Beggars | Winningest |
| Mar 14, 3:34 AM | wyambezi | --- | Winningest |
| Mar 08, 9:34 PM | granpa46 | Wise & Winsome Night Owls | Winningest |
| Mar 07, 9:34 AM | rosiegreer | The British | Winningest |
| Mar 03, 3:34 PM | fatherpat | Old Farts | Winningest |
| Feb 21, 9:35 PM | StephenFoster | Old Farts | Winningest |
| Feb 10, 3:34 PM | chessart | Old Farts | Winningest |
| Jan 28, 9:34 PM | Pennstatersdad | All 50 States | Winningest |
| Jan 28, 3:34 AM | alanwong5 | The Moops | Winningest |
| Jan 22, 3:34 PM | kevalex34 | The Cat People | Winningest |
| Jan 19, 3:35 AM | Wanderess | Worldwide Wizards | Winningest |
| Jan 19, 3:35 AM | Joekirby | --- | Winningest |
| Jan 17, 3:34 PM | Shadman11 | The Internationals | Winningest |
| Jan 11, 9:34 AM | BrightonDragon | Old Farts | Winningest |
| Jan 10, 9:35 PM | Lpez | Triviabiz | Winningest |
| Jan 07, 3:34 PM | Jorgy4 | Canadian Players | Winningest |
| Jan 01, 3:35 PM | nerzack | European Players | Winningest |
| Dec 24, 3:35 AM | Ehmer1 | Midwest USA Players | Winningest |
| Dec 22, 9:34 PM | icequeen3 | --- | Winningest |
| Dec 21, 3:35 PM | DesertDon | The Devious Demons | Winningest |
| Dec 17, 9:34 PM | JJs616 | The Homo Sapiens | Winningest |
| Dec 17, 3:34 AM | Gruntasan | The Calculators | Winningest |
| Dec 06, 9:34 AM | driver88 | TV Watchers Anonymous | Winningest |
| Nov 30, 9:34 PM | catbsk | Faithful and True | Winningest |
| Nov 14, 3:34 AM | CycleGrandma | Faithful and True | Winningest |
| Nov 13, 9:34 PM | rayvendragon | The New England Alliance | Winningest |
| Nov 13, 9:34 PM | RealtorRebecca | Washingtonians | Winningest |
| Nov 07, 9:34 PM | Tiges | --- | Winningest |
| Oct 30, 3:34 AM | Waves306 | Indian Gang | Winningest |
| Oct 15, 9:34 PM | Mazee1 | THE CONSERVATIVES | Winningest |
| Oct 13, 3:35 AM | wino2 | XYPers | Winningest |
| Oct 07, 9:34 AM | orinocowomble | Writer's Block | Winningest |
| Oct 02, 9:34 PM | elvislennon | Kilted Kangas | Winningest |
| Sep 29, 3:35 AM | Lizbetha | The Devil's Advocates | Winningest |
| Sep 22, 9:34 AM | Reveler | The Calculators | Winningest |
| Sep 20, 9:34 PM | Jdeanflpa | Retired And Loving It | Winningest |
| Sep 20, 9:34 AM | chianti59 | The Bee's Knees | Winningest |
| Sep 20, 3:34 AM | umgah | British Brains | Winningest |
| Sep 12, 3:34 AM | i-a-n | Old Farts | Winningest |
| Sep 11, 9:34 PM | Traveller1982 | The British | Winningest |
| Sep 03, 9:34 AM | amarie94903 | --- | Winningest |
| Aug 22, 9:34 AM | debodun | Retired And Loving It | Winningest |
| Aug 13, 9:34 PM | leith90 | Phoenix Rising | Winningest |
| Aug 11, 9:34 AM | Gcc3663 | Yorkshire and Proud | Winningest |
| Aug 09, 9:34 AM | Pekingese | StarStruck | Winningest |