Update for 2023 for future reference.
**1a**
1998 - Yomega RB II
1999 - Spintastics Tigershark
2000 - Spintastics Tigershark
2001 - YYJ SpinFaktor
2002 - Duncan Freehand 1
2003 - YYJ Hitman
2004 - YYJ Speeder
2005 - YYJ Speeder
2006 - YYJ Speeder
2007 - YYF 888
2008 - YYF Superstar
2009 - YYR Sleipnir
2010 - YYF Northstar
2011 - TP Positron
2012 - Something Anglam
2013 - Duncan Barracuda
2014 - YYF Shutter
2015 - CLYW Borealis
2016 - C3 Radius
2017 - C3 Radius
2018 - YYF Edge Beyond
2019 - YYF Wide Angle Shutter
*2021 Online - TP Awoken Anubis?
*2022 Online - YYF Miracle
2023 - YYF Miracle
**2a**
1998 - Yomega Raider
1999 - Yomega Raider
2000 - Yomega Raider
2001 - Spintastics Spintega
2002 - Yomega Fireball
2003 - Yomega Raider
2004 - Yomega Raider
2005 - Yomega Raider
2006 - Yomega Raider
2007 - Yomega Raider
2008 - Yomega Raider
2009 - Yomega Raider
2010 - YYJ Sunset Trajectory
2011 - Yomega Raider
2012 - YYF Loop 900
2013 - Yomega Raider
2014 - Yomega Raider
2015 - Yomega Raider
2016 - YYF Loop 1080
2017 - YYF Loop 2020
2018 - YYF Loop 2020
2019 - JPL Loop Up
*2021 Online - YYF Loop 720
*2022 Online - Yomega Raider
2023 - Duncan Hornet
**3a**
2003 - YYJ Sigma Blade?
2004 - YYJ Sigma Blade?
2005 - YYJ Sigma Blade Zwei?
2006 - Buzzon Bushido
2007 - YYJ Speeder
2008 - YYR Stargazer
2009 - YYF Superstar
2010 - YYR Stargazer v2
2011 - Duncan Echo
2012 - Duncan Barracuda
2013 - Duncan Barracuda
2014 - SOMEThING Phaser
2015 - SOMEThING Phaser
2016 - SOMEThING Phaser
2017 - SOMEThING Phaser
2018 - SOMEThING Phaser
2019 - SOMEThING Phaser
*2021 Online - YYR Anomaly
*2022 Online - TP Untangle
2023 - YYR Para Autoscopy
**4a**
2003 - YYJ Aquarius
2004 - YYJ Big Ben
2005 - YYJ Aquarius
2006 - YYJ Big Yo 2
2007 - YYJ Aquarius
2008 - YYJ Big Yo 2
2009 - Shinwoo Griffin Wing
2010 - JT Kamui
2011 - YYR Maestro
2012 - YYJ Rextreme
2013 - SOMEThING Jetset EC
2014 - YYJ Rextreme 2
2015 - YYR Aeronaut
2016 - C3 Flawless
2017 - C3 Flawless
2018 - SOMEThING Jetset EG
2019 - C3 Flawless
*2021 Online - C3 Flawless
*2022 Online - C3 Flawless Air
2023 - C3 Flawless Air
**5a**
2003 - Rafael Matsunaga - Night Moves 1 (YoYoJam)
2004 - Makoto Numagami - Hitman (YoYoJam)
2005 - Maya Nakamura - Freehand Zero (Duncan)
2006 - Dana Bennett - Element X Pro (Buzz-on)
2007 - Tyler Severance - Freehand Zero (Duncan)
2008 - Takeshi Matsuura - Lyn Fury (YoYoJam)
2009 - Takuma Inoue - Leviathan 1 (Turning Point)
2010 - Takeshi Matsuura - Ai (YoYoJam)
2011 - Takeshi Matsuura - Destiny (YoYoJam)
2012 - Takeshi Matsuura - Quest (YoYoJam)
2013 - Takeshi Matsuura - Ai (YoYoJam)
2014 - Takeshi Matsuura - Leviathan 6 (Turning Point)
2015 - Jake Elliott - Atlas (YYF&YoTricks)
2016 - Takeshi Matsuura - Palpitation (Turning Point)
2017 - Takuma Inoue - Anubis (Turning Point)
2018 - Sora Ishikawa - ReMaster Galaxy (C3yoyodesign)
2019 - Hideo Ishida - Laurus (Hydrangea)
*OWYYC 2021 - Sora Ishikawa - IX (C3yoyodesign)
*OWYYC 2022 - Sora Ishikawa - Stellar IX (C3yoyodesign)
2023 - Sora Ishikawa - Stellar IX (C3yoyodesign)
Ty to Josh Yee, Sean De Los Santos, and Mable for 2a, 4a, and 5a help respectively.