I'll do it per year as well:
My top 2 tennis players per year
1919: Bill Johnston, Bill Tilden
1920: Bill Tilden, Bill Johnston
1921: Bill Tilden, Bill Johnston
1922: Bill Tilden, Bill Johnston
1923: Bill Tilden, Bill Johnston
1924: Bill Tilden, Bill Johnston
1925: Bill Tilden, Bill Johnston
1926: Rene Lacoste, Jean Borotra
1927: Rene Lacoste, Bill Tilden
1928: Henri Cochet, Rene Lacoste
1929: Henri Cochet, Rene Lacoste
1930: Henri Cochet, Bill Tilden
1931: Bill Tilden, Ellsworth Vines
1932: Ellsworth Vines, Bill Tilden
1933: Jack Crawford, Fred Perry
1934: Ellsworth Vines, Fred Perry
1935: Ellsworth Vines, Fred Perry
1936: Ellsworth Vines, Fred Perry
1937: Ellsworth Vines, Fred Perry
1938: Ellsworth Vines, Don Budge
1939: Don Budge, Ellsworth Vines
1940: Don Budge, Fred Perry
1941: Fred Perry, Bobby Riggs
1942: Don Budge, Bobby Riggs
1943: ??????
1944: Bobby Riggs, Don Budge
1945: Bobby Riggs, Don Budge
1946: Bobby Riggs, Don Budge
1947: Bobby Riggs, Jack Kramer
1948: Jack Kramer, Bobby Riggs
1949: Jack Kramer, Bobby Riggs
1950: Jack Kramer, Pancho Segura
1951: Jack Kramer, Pancho Segura
1952: Pancho Segura, Pancho Gonzales
1953: Jack Kramer, Frank Sedgman
1954: Pancho Gonzales, Frank Sedgman
1955: Pancho Gonzales, Pancho Segura
1956: Pancho Gonzales, Frank Sedgman
1957: Pancho Gonzales, Pancho Segura
1958: Pancho Gonzales, Frank Sedgman
1959: Pancho Gonzales, Lew Hoad
1960: Pancho Gonzales, Ken Rosewall
1961: Pancho Gonzales, Ken Rosewall
1962: Ken Rosewall, Lew Hoad
1963: Ken Rosewall, Rod Laver
1964: Rod Laver, Ken Rosewall
1965: Rod Laver, Ken Rosewall
1966: Rod Laver, Ken Rosewall
1967: Rod Laver, Ken Rosewall
1968: Rod Laver, Ken Rosewall
1969: Rod Laver, Tony Roche
1970: Rod Laver, Ken Rosewall
1971: John Newcombe, Stan Smith
1972: Stan Smith, Ilie Nastase
1973: Ilie Nastase, John Newcombe
1974: Jimmy Connors, John Newcombe
1975: Arthur Ashe, Jimmy Connors
1976: Jimmy Connors, Bjorn Borg
1977: Guillermo Vilas, Bjorn Borg
1978: Bjorn Borg, Jimmy Connors
1979: Bjorn Borg, John McEnroe
1980: Bjorn Borg, John McEnroe
1981: John McEnroe, Bjorn Borg
1982: Jimmy Connors, Ivan Lendl
1983: John McEnroe, Mats Wilander
1984: John McEnroe, Jimmy Connors
1985: Ivan Lendl, John McEnroe
1986: Ivan Lendl, Boris Becker
1987: Ivan Lendl, Stefan Edberg
1988: Mats Wilander, Ivan Lendl
1989: Boris Becker, Ivan Lendl
1990: Stefan Edberg, Andre Agassi
1991: Stefan Edberg, Jim Courier
1992: Jim Courier, Stefan Edberg
1993: Pete Sampras, Jim Courier
1994: Pete Sampras, Andre Agassi
1995: Pete Sampras, Andre Agassi
1996: Pete Sampras, Boris Becker
1997: Pete Sampras, Patrick Rafter
1998: Pete Sampras, Marcelo Rios
1999: Andre Agassi, Pete Sampras
2000: Gustavo Kuerten, Marat Safin
2001: Lleyton Hewitt, Gustavo Kuerten
2002: Lleyton Hewitt, Andre Agassi
2003: Andy Roddick, Roger Federer
2004: Roger Federer, Lleyton Hewitt
2005: Roger Federer, Rafael Nadal
2006: Roger Federer, Rafael Nadal
2007: Roger Federer, Rafael Nadal
2008: Rafael Nadal, Roger Federer
2009: Roger Federer, Rafael Nadal
2010: Rafael Nadal, Roger Federer
2011: Novak Djokovic, Rafael Nadal
My top 2 amateur tennis players per year
1919: Bill Johnston, Bill Tilden
1920: Bill Tilden, Bill Johnston
1921: Bill Tilden, Bill Johnston
1922: Bill Tilden, Bill Johnston
1923: Bill Tilden, Bill Johnston
1924: Bill Tilden, Bill Johnston
1925: Bill Tilden, Bill Johnston
1926: Rene Lacoste, Jean Borotra
1927: Rene Lacoste, Bill Tilden
1928: Henri Cochet, Rene Lacoste
1929: Henri Cochet, Rene Lacoste
1930: Henri Cochet, Bill Tilden
1931: Ellsworth Vines, Henri Cochet
1932: Ellsworth Vines, Henri Cochet
1933: Jack Crawford, Fred Perry
1934: Fred Perry, Jack Crawford
1935: Fred Perry, Jack Crawford
1936: Fred Perry, Gottfried von Cramm
1937: Don Budge, Gottfried von Cramm
1938: Don Budge, Bunny Austin
1939: Bobby Riggs, John Bromwich
1940: Don McNeill, Bobby Riggs
1941: Bobby Riggs, Frank Kovacs
1942: Ted Schroeder, Frank Parker
1943: Joseph Hunt, Jack Kramer
1944: Frank Parker, Bill Talbert
1945: Frank Parker, Bill Talbert
1946: Jack Kramer, John Bromwich
1947: Jack Kramer, Dinny Pails
1948: John Bromwich, Pancho Gonzales
1949: Pancho Gonzales, Ted Schroeder
1950: Budge Patty, Frank Sedgman
1951: Frank Sedgman, Dick Savitt
1952: Frank Sedgman, Jaroslav Drobny
1953: Tony Trabert, Ken Rosewall
1954: Jaroslav Drobny, Tony Trabert
1955: Tony Trabert, Ken Rosewall
1956: Lew Hoad, Ken Rosewall
1957: Lew Hoad, Ashley Cooper
1958: Ashley Cooper, Mal Anderson
1959: Alex Olmedo, Neale Fraser
1960: Neale Fraser, Rod Laver
1961: Roy Emerson, Rod Laver
1962: Rod Laver, Roy Emerson
1963: Roy Emerson, Chuck McKinley
1964: Roy Emerson, Fred Stolle
1965: Roy Emerson, Fred Stolle
1966: Fred Stolle, Manuel Santana
1967: John Newcombe, Roy Emerson
My top 2 professional tennis players per year
1927: Vinny Richards, Howard Kinsey
1928: Vinny Richards, Karel Kozeluh
1929: Karel Kozeluh, Vinny Richards
1930: Karel Kozeluh, Vinny Richards
1931: Bill Tilden, Vinny Richards
1932: Bill Tilden, Karel Kozeluh
1933: Bill Tilden, Hans Nusslein
1934: Ellsworth Vines, Hans Nusslein
1935: Ellsworth Vines, Hans Nusslein
1936: Ellsworth Vines, Hans Nusslein
1937: Ellsworth Vines, Fred Perry
1938: Ellsworth Vines, Hans Nusslein
1939: Don Budge, Ellsworth Vines
1940: Don Budge, Fred Perry
1941: Fred Perry, Dick Skeen
1942: Don Budge, Bobby Riggs
1943: ??????
1944: Bobby Riggs, Don Budge
1945: Bobby Riggs, Don Budge
1946: Bobby Riggs, Don Budge
1947: Bobby Riggs, Don Budge
1948: Jack Kramer, Bobby Riggs
1949: Jack Kramer, Bobby Riggs
1950: Jack Kramer, Pancho Segura
1951: Jack Kramer, Pancho Segura
1952: Pancho Segura, Pancho Gonzales
1953: Jack Kramer, Frank Sedgman
1954: Pancho Gonzales, Frank Sedgman
1955: Pancho Gonzales, Pancho Segura
1956: Pancho Gonzales, Frank Sedgman
1957: Pancho Gonzales, Pancho Segura
1958: Pancho Gonzales, Frank Sedgman
1959: Pancho Gonzales, Lew Hoad
1960: Pancho Gonzales, Ken Rosewall
1961: Pancho Gonzales, Ken Rosewall
1962: Ken Rosewall, Lew Hoad
1963: Ken Rosewall, Rod Laver
1964: Rod Laver, Ken Rosewall
1965: Rod Laver, Ken Rosewall
1966: Rod Laver, Ken Rosewall
1967: Rod Laver, Ken Rosewall