As of August 2018, three teams were interested in submitting bids as the league met with representatives of those unnamed clubs in Hamilton. Based on the location of the meeting and their previously-stated desire to host, the Hamilton Tiger-Cats were speculated to be one of the teams. The previous obstacle of the lawsuit over the construction of Tim Hortons Field was settled on May 31, 2018, which had prevented the Tiger-Cats from bidding on a Grey Cup game. The Tiger-Cats had previously expressed interest in submitting a bid for the 107th Grey Cup and with litigation cleared, they can move forward with bidding to host their first championship game since the 84th Grey Cup in 1996. The first club to openly confirm their plans to bid were the Saskatchewan Roughriders, as stated by the club's president and CEO, Craig Reynolds, on October 1, 2018. The game would coincide with the 110th anniversary of the club and would be the fourth time the game would be hosted in Saskatchewan, if successful. The Roughriders' new facility, Mosaic Stadium, opened in 2017 and the Roughriders last hosted the Grey Cup in 2013. On November 4, 2018, it was reported that the Montreal Alouettes were preparing a bid to see Olympic Stadium host the 2020 championship game. The Alouettes confirmed that they had representatives in Toronto on November 6, 2018 to make their presentation at the league head office to host the game. It was confirmed on November 13, 2018 that the Tiger-Cats were indeed making a bid for the game as team representatives made their presentation to the league head office in Toronto the week prior. Their Grey Cup festival concept included a downtown-centred event at venues like the Hamilton Convention Centre and Art Gallery of Hamilton. The Tiger-Cats' president of business operations, Matt Afinec, confirmed that the club had support from Hamilton's mayor, Fred Eisenberger, and that three bids for the Grey Cup game had been made. The CFL's Grey Cup director, Céline Séguin, had previously stated that the league would like to announce hosts sooner. With the previous year's game being announced 19 months prior, this game could be declared much earlier. On February 21, 2019, it was officially announced that the 2020 and 2021 Grey Cup games had been respectively awarded to Regina and Hamilton.
The 108th Grey Cup faced a possible postponement or cancellation due to the COVID-19 pandemic; on May 11, Premier Scott Moe stated that current public health orders would not allow events that constitute large gatherings, "including up to and potentially including even this fall's Grey Cup", for the foreseeable future. The 101st Grey Cup attracted $93 million in economic activity to the province. On May 20, the CFL announced that the 2020 season will not begin until at least September, and that the 108th Grey Cup and its festivities will not be hosted by Regina as a neutral site. Instead, the Grey Cup will be played at the home field of the participating team with the better regular season record. Regina will host the 110th Grey Cup as a neutral site in 2022.
