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1996 – Straight No Chaser founded at Indiana University. Edit

2006 – Ten-year anniversary of Straight No Chaser; Randy Stine uploaded videos on YouTube, including "The Twelve Days of Christmas".

2008 – Straight No Chaser signs with Atlantic Records; begins first tour.

December 18, 2008 — Straight No Chaser's first professional concert in Los Angelos, California.
2009 – Michael Itkoff and Steve Morgan leave group to be replaced by Seggie Isho and Tyler Trepp.

2010 – Songs Through The Decades shows at Harrah's.

2010 – Dan Ponce leaves, being replaced by Don Nottingham.

2012 October – Straight No Chaser hosts their first cruise, called Chasers at Sea.

2012 December – Ryan Ahlwardt leaves Straight No Chaser.

2013 February – Steve rejoins Straight No Chaser, filling Ryan's place.

2013 September – Three-day Chaser Summit at Vegas.

2017 May – Don Nottingham announces that he has left Straight No Chaser.

2017 summer – Straight No Chaser's first joint tour with Postmodern Jukebox, titled the Double Feature Tour.