I see a problem with this list, namely that it ignores butterflies. With a POD in 1970, there's plenty of time for people who in OTL remained minor figures or never entered politics in the first place to rise to prominence; conversely, the butterflies may perfectly cause prominent figures from OTL to remain obscure. In fact by 2020 it's possible for people who weren't even born in OTL to become PM.
October 25, 1972: Robert Stanfield (PC, Maj)
May 29th 1977: Edgar Benson (Lib, Maj)
September 22nd 1980: Edgar Benson (Lib, Min)
May 11th 1981: John Crosbie (PC, Min)
August 27th 1982: John Turner (Lib, Min)
February 17th 1984: John Turner (Lib, Maj)
March 21st 1988: Michael Wilson (PC, Maj)
June 16th 1992: Kim Campbell (PC, Maj)
September 16th 1996: Stephen G. Yzerman (Lib, Min)
October 12th 1999: Stephen G. Yzerman (Lib, Maj)
May 21st 2004: Jack Layton (NDP, Maj)
January 22nd 2013: Gabriel McKeon (NDP, Maj)
June 12th 2017: Richard Mercer (PC, Maj)
Oh hell no you didn't...... Rick Mercer as PM?!Why?! For the love of God why?! That man is one of the best comedians on Earth and you made him into a politician, and a Conservative one at that?!?!?!
October 25, 1972: Robert Stanfield (PC, Maj)
May 29th 1977: Edgar Benson (Lib, Maj)
September 22nd 1980: Edgar Benson (Lib, Min)
May 11th 1981: John Crosbie (PC, Min)
August 27th 1982: John Turner (Lib, Min)
February 17th 1984: John Turner (Lib, Maj)
March 21st 1988: Michael Wilson (PC, Maj)
June 16th 1992: Kim Campbell (PC, Maj)
September 16th 1996: Stephen G. Yzerman (Lib, Min)
October 12th 1999: Stephen G. Yzerman (Lib, Maj)
May 21st 2004: Jack Layton (NDP, Maj)
July 19, 2009: Scott Brison (PC, Maj)
January 22nd 2013: Gabriel McKeon (NDP, Maj)
June 12th 2017: Richard Mercer (PC, Maj)
November 12th, 2019: Richard Mercer (PC, Min)
Oh hell no you didn't...... Rick Mercer as PM?!Why?! For the love of God why?! That man is one of the best comedians on Earth and you made him into a politician, and a Conservative one at that?!?!?!