The following is a list of transfers related to the 2019 Canadian Premier League season. All transfers made during, or prior to the 2019 season are included here.
All clubs without a flag are members of the Canadian Premier League.
The 2019 Canadian Premier League season was the inaugural season of the Canadian Premier League, the top level of Canadian professional soccer. The regular season began on April 27 and ended on October 19, with seven teams competing. The CPL's inaugural match took place between Forge FC and York9 at Tim Hortons Field on April 27, 2019, which ended in a 1–1 draw.
The 2019 Valour FC season was the first season in the club's history, as well as the first season in Canadian Premier League history.
The 2019 Forge FC season was the first season in the club's history, as well as first season in Canadian Premier League history. On April 27, 2019, Forge FC hosted York9 FC in the inaugural CPL match at Tim Hortons Field. During the season, Forge also participated in the Canadian Championship, CONCACAF League, and the Canadian Premier League Finals.
The 2019 Cavalry FC season was the first season in the club's history, as well as the first season in Canadian Premier League history.
The 2019 FC Edmonton season was the eighth season in the club's history, as well as the first season in Canadian Premier League history.
The 2019 HFX Wanderers FC season was the first season in the club's history having been founded on 5 May 2018, as well as the first season in Canadian Premier League (CPL) history. Stephen Hart was the club's first manager, with the team playing at Wanderers Grounds. The season covers the period from 1 November 2018 through to 31 October 2019. Hart, like his peers in the CPL, built a squad from the ground up, and made use of all available mechanisms for player recruitment: the CPL Open Trials, the U-Sports Draft, and benefiting from his domestic and international connections, particularly from his native Trinidad & Tobago.
The 2019 Pacific FC season was the first in the club's history, as well as first season in Canadian Premier League history.
The 2019 York9 FC season was the first season in the club's history, as well as first season in Canadian Premier League history.
The 2020 York9 FC season was the second season in the club's history and the last under the York9 name.
The 2020 HFX Wanderers FC season was the second season in the club's history, as well as second season in Canadian Premier League history. The Wanderers were CPL runners-up, having been defeated by Forge FC in the 2020 CPL Final.
The 2020 FC Edmonton season was the club's ninth competitive season as well as their second in the Canadian Premier League. In their previous season, FC Edmonton finished 3rd in the Spring season and 6th in the Fall season, failing to qualify for the finals.
The 2020 Cavalry FC season was the second season in the history of Cavalry FC. In the previous season, Cavalry won both the spring and fall seasons but lost in the finals to Forge FC.
The 2020 Valour FC season was the second season in the club's history, as well as the second season in Canadian Premier League history.
The 2021 York United FC season was the third season in the club's history and the first as York United.
The 2021 Pacific FC season was the third season in the history of Pacific FC, as well as third in the Canadian Premier League. In addition to the domestic league, the club competed in the Canadian Championship.
The 2022 Valour FC season was the fourth season in the history of Valour FC. In addition to the Canadian Premier League, the club competed in the Canadian Championship.
The club has also announced that defender Nestor Navia will no longer be joining the club for the 2019 season due to personal reasons.