Battle of the Anglosphere leaders since WWII

[Phony Moderate]

Who would get your vote in each of these contests?

1945: Harry S. Truman (USA-Democratic) vs. Winston Churchill (UK-Conservative) vs. Mackenzie King (CAN-Liberal) vs. Ben Chifley (AUS-Labor) vs. Peter Fraser (NZ-Labour)

1950: Harry S. Truman (USA-Democratic) vs. Clement Attlee (UK-Labour) vs. Louis St. Laurent (CAN-Liberal) vs. Robert Menzies (AUS-Liberal) vs. Sidney Holland (NZ-National)

1955: Dwight D. Eisenhower (USA-Republican) vs. Anthony Eden (UK-Conservative) vs. Louis St. Laurent (CAN-Liberal) vs. Robert Menzies (AUS-Liberal) vs. Sidney Holland (NZ-National)

1960: Dwight D. Eisenhower (USA-Republican) vs. Harold Macmillan (UK-Conservative) vs. John Diefenbaker (CAN-Progressive Conservative) vs. Robert Menzies (AUS-Liberal) vs. Walter Nash (NZ-Labour)

1965: Lyndon B. Johnson (USA-Democratic) vs. Harold Wilson (UK-Labour) vs. Lester B. Pearson (CAN-Liberal) vs. Robert Menzies (AUS-Liberal) vs. Keith Holyoake (NZ-National)

1970: Richard Nixon (USA-Republican) vs. Edward Heath (UK-Conservative) vs. Pierre Trudeau (CAN-Liberal) vs. John Gorton (AUS-Liberal) vs. Keith Holyoake (NZ-National)

1975: Gerald Ford (USA-Republican) vs. Harold Wilson (UK-Labour) vs. Pierre Trudeau (CAN-Liberal) vs. Gough Whitlam (AUS-Labor) vs. Bill Rowling (NZ-Labour)

1980: Jimmy Carter (USA-Democratic) vs. Margaret Thatcher (UK-Conservative) vs. Pierre Trudeau (CAN-Liberal) vs. Malcolm Fraser (AUS-Liberal) vs. Robert Muldoon (NZ-National)

1985: Ronald Reagan (USA-Republican) vs. Margaret Thatcher (UK-Conservative) vs. Brian Mulroney (CAN-Progressive Conservative) vs. Bob Hawke (AUS-Labor) vs. David Lange (NZ-Labour)

1990: George H. W. Bush (USA-Republican) vs. Margaret Thatcher (UK-Conservative) vs. Brian Mulroney (CAN-Progressive Conservative) vs. Bob Hawke (AUS-Labor) vs. Geoffrey Palmer (NZ-Labour)

1995: Bill Clinton (USA-Democratic) vs. John Major (UK-Conservative) vs. Jean Chretien (CAN-Liberal) vs. Paul Keating (AUS-Labor) vs. Jim Bolger (NZ-National)

2000: Bill Clinton (USA-Democratic) vs. Tony Blair (UK-Labour) vs. Jean Chretien (CAN-Liberal) vs. John Howard (AUS-Liberal) vs. Helen Clark (NZ-Labour)

2005: George W. Bush (USA-Republican) vs. Tony Blair (UK-Labour) vs. Paul Martin (CAN-Liberal) vs. John Howard (AUS-Liberal) vs. Helen Clark (NZ-Labour)

2010: Barack Obama (USA-Democratic) vs. David Cameron (UK-Conservative) vs. Stephen Harper (CAN-Conservative) vs. Julia Gillard (AUS-Labor) vs. John Key (NZ-National)

(The leader in the years in which there were multiple leaders (of the nation in question) is determined by which one was in power the longest during said year.)

[Phony Moderate]

1945: Harry S. Truman (USA-Democratic) vs. Winston Churchill (UK-Conservative) vs. Mackenzie King (CAN-Liberal) vs. Ben Chifley (AUS-Labor) vs. Peter Fraser (NZ-Labour)

1950: Harry S. Truman (USA-Democratic) vs. Clement Attlee (UK-Labour) vs. Louis St. Laurent (CAN-Liberal) vs. Robert Menzies (AUS-Liberal) vs. Sidney Holland (NZ-National)

1955: Dwight D. Eisenhower (USA-Republican) vs. Anthony Eden (UK-Conservative) vs. Louis St. Laurent (CAN-Liberal) vs. Robert Menzies (AUS-Liberal) vs. Sidney Holland (NZ-National)

1960: Dwight D. Eisenhower (USA-Republican) vs. Harold Macmillan (UK-Conservative) vs. John Diefenbaker (CAN-Progressive Conservative) vs. Robert Menzies (AUS-Liberal) vs. Walter Nash (NZ-Labour)

1965: Lyndon B. Johnson (USA-Democratic) vs. Harold Wilson (UK-Labour) vs. Lester B. Pearson (CAN-Liberal) vs. Robert Menzies (AUS-Liberal) vs. Keith Holyoake (NZ-National)

1970: Richard Nixon (USA-Republican) vs. Edward Heath (UK-Conservative) vs. Pierre Trudeau (CAN-Liberal) vs. John Gorton (AUS-Liberal) vs. Keith Holyoake (NZ-National)

1975: Gerald Ford (USA-Republican) vs. Harold Wilson (UK-Labour) vs. Pierre Trudeau (CAN-Liberal) vs. Gough Whitlam (AUS-Labor) vs. Bill Rowling (NZ-Labour)

1980: Jimmy Carter (USA-Democratic) vs. Margaret Thatcher (UK-Conservative) vs. Pierre Trudeau (CAN-Liberal) vs. Malcolm Fraser (AUS-Liberal) vs. Robert Muldoon (NZ-National)

1985: Ronald Reagan (USA-Republican) vs. Margaret Thatcher (UK-Conservative) vs. Brian Mulroney (CAN-Progressive Conservative) vs. Bob Hawke (AUS-Labor) vs. David Lange (NZ-Labour)

1990: George H. W. Bush (USA-Republican) vs. Margaret Thatcher (UK-Conservative) vs. Brian Mulroney (CAN-Progressive Conservative) vs. Bob Hawke (AUS-Labor) vs. Geoffrey Palmer (NZ-Labour)

1995: Bill Clinton (USA-Democratic) vs. John Major (UK-Conservative) vs. Jean Chretien (CAN-Liberal) vs. Paul Keating (AUS-Labor) vs. Jim Bolger (NZ-National)

2000: Bill Clinton (USA-Democratic) vs. Tony Blair (UK-Labour) vs. Jean Chretien (CAN-Liberal) vs. John Howard (AUS-Liberal) vs. Helen Clark (NZ-Labour)

2005: George W. Bush (USA-Republican) vs. Tony Blair (UK-Labour) vs. Paul Martin (CAN-Liberal) vs. John Howard (AUS-Liberal) vs. Helen Clark (NZ-Labour)

2010: Barack Obama (USA-Democratic) vs. David Cameron (UK-Conservative) vs. Stephen Harper (CAN-Conservative) vs. Julia Gillard (AUS-Labor) vs. John Key (NZ-National)

[Phony Moderate]

2000 seems to be the only instance on this list.  

It would not be, as, generally speaking, the term 'liberal' is not a synonym for 'left-wing' outside of the U.S, and John Howard is arguably the most right-wing leader of anyone listed here.