Season 0 of How It Should Have Ended premiered on February 28, 2006.

Season 1 of How It Should Have Ended premiered on April 23, 2005.

Season 2 of How It Should Have Ended premiered on September 30, 2009.

Season 3 of How It Should Have Ended premiered on January 14, 2011.

Season 4 of How It Should Have Ended premiered on January 19, 2012.

Season 5 of How It Should Have Ended premiered on January 3, 2013.

Season 6 of How It Should Have Ended premiered on January 15, 2014.

Season 7 of How It Should Have Ended premiered on February 12, 2015.

Season 8 of How It Should Have Ended premiered on February 9, 2016.

Season 9 of How It Should Have Ended premiered on January 31, 2017.

Season 10 of How It Should Have Ended premiered on January 9, 2018.

Season 11 of How It Should Have Ended premiered on January 31, 2019.

Season 12 of How It Should Have Ended premiered on January 15, 2020.

Season 13 of How It Should Have Ended premiered on February 11, 2021.

Season 14 of How It Should Have Ended premiered on March 4, 2022.

Season 15 of How It Should Have Ended premiered on February 22, 2023.

Season 16 of How It Should Have Ended premiered on February 8, 2024.

Season 17 of How It Should Have Ended premiered on February 6, 2025.