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In June 2010, at the 2010 Annual General Meeting of the Engineering Students Societies' Council of Ontario ([https://www.essco.ca/ ESSCO]), the Presidents and VP Externals of the engineering societies of the University of Waterloo (Scott Rankin/Tim Bandura and Leah Allen/Kevin Ling), McMaster University (Kyle Heywood/Evan Stevens), and University of Toronto (Kevin Siu/Mauricio Curbelo) along with the incoming and outgoing presidents of ESSCO (Spencer McEwan and Alessia Danelon) discussed a friendly competition to promote spirit and inter-school rivalry.
The idea, introduced to the three engineering societies by the ESSCO executives, was based loosely on the "Cup Run" organized between the University of Alberta and University of Calgary Engineering Students' Societies. The Alberta version of the Cup Run involved the two universities taking turns hosting the Alberta Cup, which allowed them to call the other engineering society at a time of their choosing - if the opposing engineering society arrived within four hours, they were granted free drinks at the hosts' expense.<ref>Yasser Al-Khder,
"The Cup Will Be Up". ''The Iron Warrior'' (2 Nov 2011) http://iwarrior.uwaterloo.ca/2011/11/02/12515/the-cup-will-be-up/</ref>
By late June 2019, efforts began to draft a document outlining the rules and regulations involving the engineering societies of all three schools. Scott Rankin proposed the first draft as a mock "motion" before ESSCO, titled ''"[[:File:Motion Three Schools one cup.pdf|Three Schools One Cup]]''". On July 5, 2010, the three participating engineering societies agreed to and enacted ''[[:File:The Gran Turismo Accord.pdf|The Gran Turismo Accord]]'', defining the initial rules for ''The Cannonball Run''.
Fall2018TDC.jpg|thumb|Skule in possession of the Cup after winning it in July 2018