Who won the most games against the Chicago Cubs?

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Overall records
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Most wins, career

48 Warren Spahn (7/19/1946-9/12/1965[g2])
41 Steve Carlton (6/2/1967-6/14/1984)
38 Paul Derringer (5/3/1931-9/22/1942[g1])
38 Burleigh Grimes (8/15/1919-9/7/1931[g2])
36 Robin Roberts (6/27/1948[g2]-5/18/1966[g2])
36 Rip Sewell (5/27/1939-7/9/1949)
34 Dazzy Vance (5/22/1922-9/3/1933)
33 Carl Hubbell (7/31/1928[g1]-7/28/1942[g1])
31 Harry Brecheen (4/29/1943-6/27/1951)
30 Don Drysdale (5/1/1957-7/27/1969)
28 Bob Gibson (9/12/1959-9/27/1974)
28 Dwight Gooden (5/1/1984-6/22/1998)
28 Ken Raffensberger (7/2/1944[g2]-7/10/1953[g1])
27 Bob Friend (8/11/1951[g2]-6/24/1966)
27 Phil Niekro (7/4/1967[g1]-8/19/1983)
25 Lew Burdette (8/16/1953[g1]-8/5/1965)
25 Harry Gumbert (6/27/1936-5/16/1948)
25 Curt Simmons (6/3/1948-8/23/1965)
24 Russ Meyer (6/14/1949-9/9/1955[g2])
24 Eppa Rixey (7/9/1919[g2]-7/29/1930)
24 Tom Seaver (4/20/1967-9/24/1983)
24 Bucky Walters (5/18/1935-8/26/1944)

Most wins, relief

18 Roy Face (4/30/1953-6/22/1969[g2])
12 Mike Marshall (9/9/1970-8/19/1975)
12 Lindy McDaniel (5/27/1956[g1]-6/23/1966)
12 Kent Tekulve (8/8/1979-7/31/1987)
11 Dave Giusti (5/30/1962-9/23/1976)
10 Turk Farrell (5/3/1957-6/6/1967[g2])
10 Roger McDowell (8/9/1985-6/26/1993)
10 Don McMahon (9/22/1957-5/20/1971)
10 Stu Miller (6/21/1957-4/27/1962)

Most wins, 1910s

1919
5 Jesse Barnes5
5 Wilbur Cooper5
4 Dick Rudolph4
4 Slim Sallee4
3 Rube Benton3
3 Ray Fisher3
3 Lee Meadows3
3 Art Nehf3
3 Jeff Pfeffer3

Most wins, 1920s

1920192119221923192419251926192719281929
30 Burleigh Grimes2311235355
27 Dazzy Vance  52542153
21 Eppa Rixey2223232131
18 Art Nehf333242 1  
18 Bill Sherdel2331 31221
17 Johnny Morrison 3 4422  2
17 Jimmy Ring432422    
16 Pete Donohue  23332111

Most wins, 1930s

1930193119321933193419351936193719381939
32 Paul Derringer 421246445
25 Carl Hubbell2223224332
16 Red Lucas123312112 
15 Van Mungo 113214111
13 Ed Brandt 2123 131 
13 Dizzy Dean  331321  
13 Freddie Fitzsimmons321221  2 
13 Fred Frankhouse231311 2  
13 Hal Schumacher 114321  1

Most wins, 1940s

1940194119421943194419451946194719481949
35 Rip Sewell2546123273
27 Harry Brecheen   1346544
20 Kirby Higbe2552  33  
18 Johnny Vander Meer 323  3241
17 Max Lanier5223311   
15 Johnny Sain  2   1453
14 Mort Cooper2223212   
14 Ken Raffensberger    2 2226

Most wins, 1950s

1950195119521953195419551956195719581959
29 Robin Roberts2425324223
23 Warren Spahn23131 3424
20 Russ Meyer123563    
18 Jim Hearn252311211 
18 Don Newcombe34  136  1
16 Lew Burdette   2233123
16 Murry Dickson1323124   
16 Gerry Staley2653      

Most wins, 1960s

1960196119621963196419651966196719681969
23 Don Drysdale4134221321
18 Bob Gibson 212325 21
18 Jim Maloney 223431 21
17 Juan Marichal 112223231
16 Chris Short311 323 3 
15 Sandy Koufax1411233   
15 Jim O'Toole441 4 2   
14 Ray Sadecki23223  11 
14 Warren Spahn3343 1    

Most wins, 1970s

1970197119721973197419751976197719781979
20 Steve Carlton2231312312
19 Phil Niekro4131 22132
14 Jerry Koosman3 13214   
12 Dock Ellis2143 2    
12 Bob Forsch    2422 2
12 Mike Marshall114132    
12 Tom Seaver11212112 1
12 Don Sutton1  11142 2

Most wins, 1980s

1980198119821983198419851986198719881989
18 Dwight Gooden    352323
14 Steve Carlton33341     
13 Bill Gullickson21221212  
12 Rick Rhoden 111324   
11 Rick Reuschel     23141
11 Kent Tekulve23 11 22  
10 Joaquin Andujar123 21  1 
10 Steve Rogers2134      
10 Nolan Ryan111 221 2 
10 Mike Scott 111 221 2

Most wins, 1990s

1990199119921993199419951996199719981999
13 John Smoltz22311211  
12 Andy Benes 322 11111
12 Tom Glavine 222122 1 
11 Bob Tewksbury22132 1   
10 Doug Drabek3221  11  
10 Dwight Gooden41121   1 
10 Jose Rijo331111    
8 Pete Harnisch 2 22   2 
8 Bobby Jones   11132  
8 Chan Ho Park      2312
8 Mark Portugal2  2 22   
8 Shane Reynolds    221 12

Most wins, 2000s

20002001200220032004200520062007200820092010
14 Roy Oswalt 14 2211111
10 Chris Carpenter    421  21
10 Aaron Harang    1313 11
10 Matt Morris 3231  1   
10 Brett Myers  11 12 2 3
10 Ben Sheets 3211  21  
9 Bronson Arroyo      4 3 2
9 Doug Davis   11221 2 

Fewest days to win 8 games

351 Vinegar Bend Mizell (6/8/1960-5/24/1961)
359 Joe Hatten (9/17/1946-9/10/1947)
361 Rip Sewell (4/30/1948-4/25/1949)
365 Vinegar Bend Mizell (4/19/1960-4/18/1961)
365 Rip Sewell (4/20/1948-4/19/1949)

Fewest days to win 7 games

135 Joe Hatten (4/29/1947, 5/18/1947, 6/6/1947, 6/18/1947, 7/12/1947[g1], 7/28/1947, 9/10/1947)
146 Rip Sewell (4/20/1948, 4/30/1948, 7/4/1948[g1], 8/11/1948, 8/19/1948, 9/5/1948[g1], 9/12/1948)
157 Vinegar Bend Mizell (4/19/1960, 6/8/1960, 6/24/1960, 7/29/1960, 8/9/1960, 9/9/1960, 9/22/1960[g2])
296 Rip Sewell (7/4/1948[g1]-4/25/1949)
315 Joe Hatten (9/17/1946-7/28/1947)
315 Vinegar Bend Mizell (6/8/1960-4/18/1961)

Fewest days to win 6 games

91 Joe Hatten (4/29/1947, 5/18/1947, 6/6/1947, 6/18/1947, 7/12/1947[g1], 7/28/1947)
103 Ken Raffensberger (5/30/1950[g1], 6/30/1950, 7/9/1950[g1], 8/8/1950[g1], 8/17/1950, 9/9/1950[g1])
107 Vinegar Bend Mizell (6/8/1960, 6/24/1960, 7/29/1960, 8/9/1960, 9/9/1960, 9/22/1960[g2])
116 Joe Hatten (5/18/1947, 6/6/1947, 6/18/1947, 7/12/1947[g1], 7/28/1947, 9/10/1947)
121 Russ Meyer (5/5/1954, 6/5/1954[g1], 6/19/1954, 7/18/1954, 7/28/1954, 9/2/1954)
131 Don Newcombe (5/8/1956, 5/20/1956[g2], 7/15/1956, 7/29/1956[g1], 8/28/1956[g1], 9/15/1956)
136 Rip Sewell (4/21/1943, 4/25/1943, 5/1/1943, 6/15/1943, 6/24/1943, 9/3/1943)
136 Rip Sewell (4/30/1948, 7/4/1948[g1], 8/11/1948, 8/19/1948, 9/5/1948[g1], 9/12/1948)
137 Bubba Church (5/6/1951[g1], 5/19/1951, 6/7/1951, 7/22/1951[g2], 7/27/1951, 9/19/1951)
139 Rip Sewell (4/20/1948, 4/30/1948, 7/4/1948[g1], 8/11/1948, 8/19/1948, 9/5/1948[g1])
144 Paul Derringer (4/17/1936, 5/27/1936, 6/29/1936, 8/16/1936[g2], 8/22/1936, 9/7/1936[g1])
144 Vinegar Bend Mizell (4/19/1960, 6/8/1960, 6/24/1960, 7/29/1960, 8/9/1960, 9/9/1960)
153 Ken Raffensberger (4/28/1949, 5/28/1949, 7/6/1949, 8/14/1949[g1], 8/21/1949[g2], 9/27/1949)
162 Harry Brecheen (4/20/1946, 5/29/1946, 7/5/1946, 9/5/1946, 9/23/1946, 9/28/1946)
164 Gerry Staley (4/20/1951, 4/27/1951, 7/4/1951, 9/5/1951[g2], 9/23/1951[g2], 9/30/1951[g2])

Fewest days to win 5 games

65 Rip Sewell (4/21/1943, 4/25/1943, 5/1/1943, 6/15/1943, 6/24/1943)
71 Hank Borowy (5/12/1949, 5/21/1949, 6/5/1949[g1], 6/15/1949[g2], 7/21/1949)
71 Rip Sewell (7/4/1948[g1], 8/11/1948, 8/19/1948, 9/5/1948[g1], 9/12/1948)
72 Joe Hatten (5/18/1947, 6/6/1947, 6/18/1947, 7/12/1947[g1], 7/28/1947)
72 Dave Koslo (5/17/1947, 6/3/1947, 6/25/1947, 7/15/1947, 7/27/1947)
72 Ken Raffensberger (6/30/1950, 7/9/1950[g1], 8/8/1950[g1], 8/17/1950, 9/9/1950[g1])

Fewest days to win 4 games

33 Rip Sewell (8/11/1948, 8/19/1948, 9/5/1948[g1], 9/12/1948)
35 Hank Borowy (5/12/1949, 5/21/1949, 6/5/1949[g1], 6/15/1949[g2])
36 Erv Brame (8/3/1930, 8/27/1930, 9/5/1930, 9/7/1930)
44 Johnny Sain (6/10/1947, 6/21/1947, 6/22/1947, 7/23/1947)
46 Robin Roberts (6/17/1956[g1], 7/18/1956[g1], 7/30/1956[g1], 8/1/1956)

Fewest days to win 3 games

8 Dale Murray (9/19/1975, 9/21/1975, 9/26/1975)
9 Mike Marshall (8/1/1972, 8/3/1972[g1], 8/9/1972)
11 Rip Sewell (4/21/1943, 4/25/1943, 5/1/1943)
12 Erv Brame (8/27/1930, 9/5/1930, 9/7/1930)
12 Jerry Reuss (8/17/1982, 8/18/1982, 8/28/1982)
13 Johnny Sain (6/10/1947, 6/21/1947, 6/22/1947)

Fewest days to win 2 games

1 Ted Abernathy (6/23/1968[g1], 6/23/1968[g2])
1 Ralph Branca (7/10/1947[g1], 7/10/1947[g2])
1 Willard Hunter (8/23/1964[g1], 8/23/1964[g2])
1 Howie Krist (6/27/1943[g1], 6/27/1943[g2])
1 Ed Roebuck (7/31/1957[g1], 7/31/1957[g2])
1 Gerry Staley (7/5/1948[g1], 7/5/1948[g2])
1 Bill Voiselle (6/17/1948[g1], 6/17/1948[g2])
2 Darrel Akerfelds (6/15/1990[g1], 6/16/1990)
2 Max Butcher (9/1/1937, 9/2/1937)
2 Scott Cassidy (5/5/2006, 5/6/2006)
2 Danny Darwin (9/1/1986, 9/2/1986)
2 Fred Frankhouse (6/24/1933, 6/25/1933[g2])
2 Ryan Franklin (9/18/2009, 9/19/2009)
2 Wayne Granger (8/1/1970, 8/2/1970)
2 Danny Graves (4/8/2000, 4/9/2000)
2 Jesse Haines (7/29/1933, 7/30/1933[g2])
2 Billy Koch (6/27/2003, 6/28/2003)
2 Vern Law (7/24/1965, 7/25/1965[g1])
2 Al McBean (8/14/1964[g1], 8/15/1964)
2 Alan Mills (5/16/2000, 5/17/2000)
2 Justin Miller (7/25/2008, 7/26/2008)
2 Greg Minton (7/19/1983, 7/20/1983)
2 Phil Paine (5/11/1958[g2], 5/12/1958)
2 Dan Plesac (9/27/1996[g1], 9/28/1996)
2 Ken Raffensberger (8/16/1947, 8/17/1947[g2])
2 Jerry Reuss (8/17/1982, 8/18/1982)
2 Johnny Sain (6/21/1947, 6/22/1947)
2 Ron Taylor (6/22/1970, 6/23/1970)
2 Derrick Turnbow (5/4/2005, 5/5/2005)
2 Bucky Walters (7/8/1938, 7/9/1938)
2 Mitch Williams (8/6/1991, 8/7/1991)

Longest drought between wins

5412 Rick Sutcliffe (8/31/1979-6/26/1994)
5137 Joe Heving (5/9/1931-6/2/1945)
4845 Pedro Martinez (5/6/1996-8/12/2009)
4725 Mike Stanton (7/9/1992-6/17/2005)
4368 Dutch Leonard (8/14/1935[g2]-7/31/1947)
4338 Darold Knowles (6/2/1966-4/19/1978)
4326 Dick Hall (8/1/1955-6/6/1967[g1])
4276 Tim Wakefield (9/26/1993[g2]-6/12/2005)
3757 Charlie Leibrandt (5/4/1980[g1]-8/18/1990)
3673 Omar Olivares (6/28/1991-7/19/2001)

Includes all games played between 1919 and 2010.
The information used here was obtained free of charge from and is copyrighted by Retrosheet. Interested parties may contact Retrosheet at "www.retrosheet.org".