2009

- August 30th - Weekly Facilitated Chat Room Discussions introduced.
- July 31st - New Articles system opened.
- July 28th - Sissa left the Administration.
- May 1st - TeenHelp rebranded with new "human" theme.
- April 19th - New Donations system opened.
- April 8th - TeenHelp reached 10,000 threads.
- April 5th - New HelpLINK system opened.
- April 1st - TeenHelp reached 100,000 posts.
- March 27th - TeenHelp reached 5,000 members.
- February 17th - TeenHelp reached 5,000 threads.
- February 15th - TeenHelp reached 50,000 posts. New Staff Application system opened.
- February 11th - TeenHelp underwent a major software upgrade.
- February 4th - TeenHelp moved to a new server. Email functions restored.
- January 12th - Contact Center reintroduced.
- January 11th - TeenHelp reached 1,000 members, 1,000 threads and 10,000 posts.
- January 7th - Videos system reintroduced.
- January 6th - New Main Site opened. Live Help system reintroduced. Blogs system reintroduced. Articles system reintroduced.
- January 5th - TeenHelp is restarted by Rob, Mel, Sissa and Winston. All peripheral features are disabled and all statistics are reset. Chat Room system reintroduced.

2008

- December 30th (approx.) - TeenHelp suffers major data loss. Voltar left the Administration.
- December 23rd - TeenHelp is taken offline.
- December 12th - fluffyhelen left the Administration.
- November 24th - Videos system opened.
- November 8th - New Chat Room system opened.
- September 16th - Mel joined the Administration.
- September 12th (approx.) - Maddox left the Administration.
- August 12th (approx.) - New Chat Room and Blog systems opened.
- August 7th (approx.) - New Arcade system opened.
- July 30th - TeenHelp celebrated its 10th anniversary.
- June 24th (approx.) - New Contact Center opened.
- June 13th (approx.) - TeenHelp underwent a major software upgrade.
- May 12th (approx.) - TeenHelp's mentor team have made 50,000 replies through HelpLINK.
- March 30th (approx.) - TeenHelp moved to a new server.
- February 20th (approx.) - TeenHelp reached 50,000 members.
- January 17th (approx.) - TeenHelp reached 1,000,000 posts.

2007

- November 28th (approx.) - TeenHelp reached 100,000 threads.
- October 5th - PureMorning left the Administration.
- July 30th - Kerri left the Administration.
- July 1st (approx.) - TeenHelp registered as as a not-for-profit charitable organisation in the United States of the America.
- June 30th - Dara (PureMorning) and Sissa joined the Administration.
- June 21st - Rob N joined the Administration.
- June 14th (approx.) - Kerri joined the Administration.
- June 3rd - Avatar first issue released.
- May 22nd - TeenHelp rebranded with new "bubble" logo, replacing the archaic circular arrow theme. Various other images replaced with a similar theme shortly thereafter.
- May 15th (approx.) - David (Voltar) joined the Administration.
- April 28th - Elliot (Maddox) joined the Administration.
- April 24th - SimplyRob left the Administration.
- March 15th - TeenHelp moved to a new server.

2006

- November 26th - TeenHelp moved to a new server.
- May 31st - TeenHelp Instant Messenger (beta) system opened.
- May 1st - Image Hosting system opened.
- April 24th - TeenHelp complies fully with COPPA laws. People under the age of thirteen are allowed to register.

2005

- October 28th - Donation system opened.
- October 11th - Infraction system opened.
- October 3rd - New Staff Application system opened.
- September 26th - New forum-integrated HelpLINK system opened.
- June 17th - TeenHelp reached 10,000 members.
- June 1st - Live Help system opened.
- March 29th - TeenHelp reached 100,000 posts.
- January 23rd (approx.) - Dustin left the Administration.
- January 19th - Journal system opened.

2004

- December 9th - Rob W (SimplyRob) joined the Administration.
- December 7th (approx.) - Jake left the Administration.
- September 1st (approx.) - Dustin joined the Administration.
- August 8th - New Chat Room system opened.
- August 2nd - New HelpLINK system opened.
- July 4th - TeenHelp Support Groups (Forums) restarted on vBulletin (previously Invision Power Board) by Helen (fluffyhelen), Jake and Winston. HelpingTeens split off from TeenHelp.
- June 16th - TeenHelp sold to Winston Cheng.

2003

- September 7th - New theme launched.
- January 6th - TeenHelp sold to Mike Fox.

2002

- December 20th - TeenHelp sold to Greg Harvey.

2001

- June 15th - New theme launched.

2000

- December 27th - First Support Groups (Forums) opened.
- July 26th - First primitive automated HelpLINK system opened.
- March 8th - First Chat Room system opened.
- February 19th - New "millennium edition" theme launched.

1999

1998

- July 13th - TeenHelp founded by Branden Thomas.