| class="wikitable" width=70% style=text-align:center;"
!Year
!Winner
!Nominees
!Ref. |
| 2000
| Jessica Simpson
|
| [{{cite web|url=http://www.hollywood.com/static/2000-teen-choice-awards|title=2000 Teen Choice Awards|publisher=Hollywood.com|date=August 6, 2000|accessdate=November 27, 2014}}] |
| 2001
|O-Town
|
| [{{cite web|url=http://www.hollywood.com/general/2001-teen-choice-awards-57162725/ |title=2001 Teen Choice Awards |publisher=Hollywood.com |date=August 12, 2001 |accessdate=May 21, 2015 |url-status=dead |archiveurl=https://web.archive.org/web/20160304094043/http://www.hollywood.com/general/2001-teen-choice-awards-57162725/ |archivedate=March 4, 2016 }}] |
| 2002
| Ashanti
|
| [{{cite web|url=http://newsok.com/2002-teen-choice-awards/article/2803593/?page=2|title=2002 Teen Choice Awards (page 2)|publisher=NewsOK|date=August 18, 2002|accessdate=October 28, 2014}}][{{cite web|url=http://www.hollywood.com/static/teen-choice-awards-2002-complete-winners-list|title=Teen Choice Awards 2002: Complete Winners List|publisher=Hollywood.com|date=August 4, 2002|accessdate=October 27, 2014}}] |
| 2003
|50 Cent
|
| [{{cite web|url=https://www.billboard.com/articles/news/70551/2003-teen-choice-awards-nominees|title=2003 Teen Choice Awards Nominees|work=Billboard|date=June 18, 2003|accessdate=May 20, 2015}}] |
| 2004
|Maroon 5
|
| [{{cite web|url=https://www.billboard.com/articles/news/67001/2004-teen-choice-awards-winners|title=2004 Teen Choice Awards Winners|work=Billboard|date=August 9, 2004|accessdate=November 19, 2014}}] |
| rowspan="4"|2005
!colspan="3"|Choice Male Breakout Artist |
| Jesse McCartney
|
| [{{cite web|url=http://www.fox.com/tca2005/nominees.htm|title=The Teen Choice Awards|publisher=FOX|accessdate=October 31, 2014|archiveurl=https://web.archive.org/web/20060108193620/http://www.fox.com/tca2005/nominees.htm|archivedate=January 8, 2006}}] |
| colspan="3"|Choice Female Breakout Artist |
|---|
| Gwen Stefani
|
| |
| rowspan="4"|2006
!colspan="3"|Choice Male Breakout Artist |
| Chris Brown
|
| [{{cite web|url=http://www.mtv.com/news/1538972/britney-introduces-k-fed-nick-lachey-scores-awkward-award-at-teen-choice-2006/|archive-url=https://web.archive.org/web/20150209024018/http://www.mtv.com/news/1538972/britney-introduces-k-fed-nick-lachey-scores-awkward-award-at-teen-choice-2006/|url-status=dead|archive-date=February 9, 2015|title=Britney Introduces K-Fed, Nick Lachey Scores 'Awkward' Award At Teen Choice 2006|last=Moss|first=Corey|work=MTV|publisher=Viacom|date=August 21, 2006|accessdate=June 27, 2016}}] |
| colspan="3"|Choice Female Breakout Artist |
|---|
| Rihanna
|
| |
| rowspan="6"|2007
!colspan="3"|Choice Male Breakout Artist |
| Akon
|
| [{{cite web|title=2007 Teen Choice Awards|url=http://awardsandwinners.com/category/teen-choice-awards/2007/|publisher=Awards and Winners|accessdate=June 18, 2014}}] |
| colspan="3"|Choice Female Breakout Artist |
|---|
| Vanessa Hudgens
|
| |
| colspan="3"|Choice Breakout Group |
|---|
| Gym Class Heroes
|
| |
| rowspan="4"|2008
!colspan="3"|Choice Breakout Artist |
| Taylor Swift
|
| [{{cite web|url=http://theenvelope.latimes.com/env-2008-teen-choice-awards-scorecard17jun17,0,2603341.htmlstory|work=Los Angeles Times|date=June 17, 2008|accessdate=August 6, 2013|title=2008 Teen Choice Awards winners and nominees|archiveurl=https://web.archive.org/web/20080912051322/http://theenvelope.latimes.com/env-2008-teen-choice-awards-scorecard17jun17,0,2603341.htmlstory|archivedate=September 12, 2008}}] |
| colspan="3"|Choice Breakout Group |
|---|
| Jonas Brothers
|
| |
| 2009
|David Archuleta
|
| [{{cite web|title=Teen Choice Awards 2009 nominees|url=http://latimesblogs.latimes.com/awards/2009/06/teen-choice-awards-2009-nominees.html|work=LA Times|accessdate=August 28, 2012|date=June 15, 2009}}][{{cite news|title=Teen Choice Awards winners - USATODAY.com|url=http://usatoday30.usatoday.com/life/people/2009-08-10-teen-choice-winners_N.htm|accessdate=16 May 2016|work=USA Today|date=10 August 2009}}] |