Players who played for the Boston Red Sox and Chicago Cubs
157 players
157 players have played for both the Boston Red Sox and the Chicago Cubs. Jon Lester spent the most seasons with the two: 9 with the Boston Red Sox and 6 with the Chicago Cubs. On a roster now: Willson Contreras, Craig Kimbrel, Aroldis Chapman, Michael Fulmer, and Alex Bregman. Every season since 1876 is on file.
| Player | Pos | BOS | CHC |
|---|---|---|---|
| Jon Lester | SP | 2006–2014 · 9 seasons | 2015–2020 · 6 seasons |
| Nomar Garciaparra | 1B | 1996–2004 · 9 seasons | 2004–2005 · 2 seasons |
| Fergie Jenkins | SP | 1976–1977 · 2 seasons | 1967–1983 · 9 seasons |
| Rich Hill | SP | 2010–2024 · 6 seasons | 2005–2008 · 4 seasons |
| Ryan Dempster | SP | 2013 · 1 season | 2004–2012 · 9 seasons |
| Bill Buckner | 1B | 1985–1990 · 3 seasons | 1977–1983 · 7 seasons |
| Lee Smith | RP | 1988–1989 · 2 seasons | 1980–1987 · 8 seasons |
| Frank Castillo | SP | 2001–2004 · 3 seasons | 1991–1996 · 6 seasons |
| Dennis Eckersley | RP | 1978–1998 · 7 seasons | 1985–1986 · 2 seasons |
| Dick Ellsworth | P | 1968 · 1 season | 1958–1966 · 8 seasons |
| Willson Contreras | 1B | 2026 · 1 season | 2016–2022 · 7 seasons |
| Troy O'Leary | LF | 1995–2001 · 7 seasons | 2003 · 1 season |
| Chico Walker | 2B | 1980–1984 · 4 seasons | 1985–1991 · 4 seasons |
| Dennis Lamp | RP | 1988–1991 · 4 seasons | 1977–1980 · 4 seasons |
| Dom Dallessandro | — | 1937 · 1 season | 1940–1947 · 7 seasons |
| Jack Russell | P | 1926–1931 · 6 seasons | 1938–1939 · 2 seasons |
| Johnny Welch | P | 1932–1935 · 4 seasons | 1926–1931 · 4 seasons |
| Ryan Brasier | RP | 2018–2023 · 6 seasons | 2025 · 1 season |
| Michael Bowden | RP | 2008–2012 · 5 seasons | 2012–2013 · 2 seasons |
| Rey Sanchez | 2B | 2002 · 1 season | 1991–1996 · 6 seasons |
| Bill Campbell | RP | 1977–1981 · 5 seasons | 1982–1983 · 2 seasons |
| Ray Culp | P | 1968–1973 · 6 seasons | 1967 · 1 season |
| Arnold Earley | P | 1960–1965 · 6 seasons | 1966 · 1 season |
| Dave Hillman | P | 1960–1961 · 2 seasons | 1955–1959 · 5 seasons |
| Jimmie Foxx | — | 1936–1941 · 6 seasons | 1944 · 1 season |
| John Lackey | SP | 2010–2014 · 4 seasons | 2016–2017 · 2 seasons |
| Felix Doubront | SP | 2010–2014 · 5 seasons | 2014 · 1 season |
| Terry Adams | RP | 2004 · 1 season | 1995–1999 · 5 seasons |
| Al Nipper | SP | 1983–1987 · 5 seasons | 1988 · 1 season |
| Steve Dillard | 2B | 1975–1977 · 3 seasons | 1979–1981 · 3 seasons |
| Tim Blackwell | C | 1974–1975 · 2 seasons | 1978–1981 · 4 seasons |
| Cal Koonce | P | 1971 · 1 season | 1962–1966 · 5 seasons |
| Frank Baumann | P | 1955–1959 · 5 seasons | 1965 · 1 season |
| Bill Henry | P | 1952–1955 · 4 seasons | 1958–1959 · 2 seasons |
| Lou Stringer | — | 1948–1950 · 3 seasons | 1941–1946 · 3 seasons |
| Rip Russell | — | 1946–1947 · 2 seasons | 1939–1942 · 4 seasons |
| Bill Fleming | P | 1940–1941 · 2 seasons | 1942–1946 · 4 seasons |
| Bernie Friberg | — | 1933 · 1 season | 1919–1924 · 5 seasons |
| Drew Pomeranz | RP | 2016–2018 · 3 seasons | 2025–2026 · 2 seasons |
| Craig Kimbrel | RP | 2016–2018 · 3 seasons | 2019–2020 · 2 seasons |
| Koji Uehara | RP | 2013–2016 · 4 seasons | 2017 · 1 season |
| David Ross | C | 2008–2014 · 3 seasons | 2015–2016 · 2 seasons |
| Bob Howry | RP | 2003 · 1 season | 2006–2010 · 4 seasons |
| Matt Clement | SP | 2005–2006 · 2 seasons | 2002–2004 · 3 seasons |
| Darren Lewis | LF | 1998–2001 · 4 seasons | 2002 · 1 season |
| Tom Gordon | RP | 1996–1999 · 4 seasons | 2001 · 1 season |
| Damon Berryhill | C | 1994 · 1 season | 1987–1990 · 4 seasons |
| Chuck Rainey | RP | 1979–1982 · 4 seasons | 1983 · 1 season |
| Mike Garman | P | 1969–1973 · 4 seasons | 1976 · 1 season |
| Carmen Fanzone | — | 1970 · 1 season | 1971–1974 · 4 seasons |
| Johnny Ostrowski | — | 1948 · 1 season | 1943–1946 · 4 seasons |
| Carl Reynolds | — | 1934–1935 · 2 seasons | 1937–1939 · 3 seasons |
| Ed Morris | P | 1928–1931 · 4 seasons | 1922 · 1 season |
| Hack Miller | — | 1918 · 1 season | 1922–1925 · 4 seasons |
| Ray Grimes | — | 1920 · 1 season | 1921–1924 · 4 seasons |
| Steve Yerkes | — | 1909–1913 · 4 seasons | 1916 · 1 season |
| Charlie Smith | P | 1910 · 1 season | 1911–1914 · 4 seasons |
| Rube Kroh | P | 1906–1907 · 2 seasons | 1908–1910 · 3 seasons |
| Duke Farrell | — | 1903–1905 · 3 seasons | 1888–1889 · 2 seasons |
| Reese McGuire | C | 2022–2024 · 3 seasons | 2025 · 1 season |
| Allen Webster | RP | 2013–2014 · 2 seasons | 2018–2019 · 2 seasons |
| Ryan Kalish | LF | 2010–2012 · 2 seasons | 2014–2016 · 2 seasons |
| Darnell McDonald | LF | 2010–2012 · 3 seasons | 2013 · 1 season |
| Marlon Byrd | RF | 2012 · 1 season | 2010–2012 · 3 seasons |
| Chad Fox | RP | 2003 · 1 season | 2005–2009 · 3 seasons |
| Julian Tavarez | RP | 2006–2008 · 3 seasons | 2001 · 1 season |
| Scott Williamson | RP | 2003–2004 · 2 seasons | 2005–2006 · 2 seasons |
| Todd Walker | 1B | 2003 · 1 season | 2004–2006 · 3 seasons |
| Bill Mueller | 3B | 2003–2005 · 3 seasons | 2001 · 1 season |
| Mark Bellhorn | 3B | 2004–2005 · 2 seasons | 2002–2003 · 2 seasons |
| Mike Remlinger | RP | 2005 · 1 season | 2003–2005 · 3 seasons |
| Ron Mahay | RP | 1997–1998 · 2 seasons | 2001–2002 · 2 seasons |
| Damon Buford | CF | 1998–1999 · 2 seasons | 2000–2001 · 2 seasons |
| Scott Fletcher | 2B | 1993–1994 · 2 seasons | 1981–1982 · 2 seasons |
| Lynn McGlothen | RP | 1972–1973 · 2 seasons | 1979–1980 · 2 seasons |
| Russ Meyer | P | 1957 · 1 season | 1946–1948 · 3 seasons |
| Mickey Owen | — | 1954 · 1 season | 1949–1951 · 3 seasons |
| Emmett O'Neill | P | 1943–1945 · 3 seasons | 1946 · 1 season |
| Bob Garbark | — | 1945 · 1 season | 1937–1939 · 3 seasons |
| Billy Rogell | — | 1925–1928 · 3 seasons | 1940 · 1 season |
| Earl Webb | — | 1930–1931 · 2 seasons | 1927–1928 · 2 seasons |
| Bill Piercy | P | 1922–1924 · 3 seasons | 1926 · 1 season |
| Pinky Pittinger | — | 1921–1923 · 3 seasons | 1925 · 1 season |
| Aroldis Chapman | RP | 2025–2026 · 2 seasons | 2016 · 1 season |
| Justin Wilson | RP | 2025 · 1 season | 2017–2018 · 2 seasons |
| Michael Fulmer | RP | 2025 · 1 season | 2023–2025 · 2 seasons |
| Chris Martin | RP | 2023–2024 · 2 seasons | 2022 · 1 season |
| Matt Dermody | RP | 2023 · 1 season | 2020–2022 · 2 seasons |
| Andrew Cashner | SP | 2019 · 1 season | 2010–2011 · 2 seasons |
| Ryan Sweeney | RF | 2012 · 1 season | 2013–2014 · 2 seasons |
| Joey Gathright | CF | 2009–2011 · 2 seasons | 2009 · 1 season |
| Eric Patterson | 2B | 2010 · 1 season | 2007–2008 · 2 seasons |
| Wade Miller | SP | 2005 · 1 season | 2006–2007 · 2 seasons |
| Geremi Gonzalez | RP | 2005 · 1 season | 1997–1998 · 2 seasons |
| Ricky Gutierrez | 2B | 2004 · 1 season | 2000–2001 · 2 seasons |
| Willie Banks | RP | 2001–2002 · 2 seasons | 1994 · 1 season |
| Rod Beck | RP | 2000–2001 · 2 seasons | 1998 · 1 season |
| Manny Alexander | SS | 2000 · 1 season | 1998–1999 · 2 seasons |
| Heathcliff Slocumb | RP | 1996 · 1 season | 1991–1992 · 2 seasons |
| Billy Hatcher | RF | 1993 · 1 season | 1984–1985 · 2 seasons |
| A. Mike Brumley | LF | 1991–1992 · 2 seasons | 1987 · 1 season |
| Calvin Schiraldi | RP | 1986–1987 · 2 seasons | 1988 · 1 season |
| Allen Ripley | SP | 1978–1979 · 2 seasons | 1982 · 1 season |
| Jack Lamabe | P | 1963–1964 · 2 seasons | 1968 · 1 season |
| Gene Mauch | — | 1956–1957 · 2 seasons | 1949 · 1 season |
| Billy Holm | — | 1945 · 1 season | 1943–1944 · 2 seasons |
| Hy Vandenberg | P | 1935 · 1 season | 1944–1945 · 2 seasons |
| Bob Barrett | — | 1929 · 1 season | 1923–1924 · 2 seasons |
| Norm McMillan | — | 1923 · 1 season | 1928–1929 · 2 seasons |
| Rudy Sommers | P | 1926–1927 · 2 seasons | 1912 · 1 season |
| Howie Fitzgerald | — | 1926 · 1 season | 1922–1924 · 2 seasons |
| Oscar Fuhr | P | 1924–1925 · 2 seasons | 1921 · 1 season |
| Dave Shean | — | 1918–1919 · 2 seasons | 1911 · 1 season |
| Tom Hughes | P | 1903 · 1 season | 1900–1901 · 2 seasons |
| Alex Bregman | 3B | 2025 · 1 season | 2026 · 1 season |
| Brad Keller | RP | 2024 · 1 season | 2025 · 1 season |
| Justin Turner | 1B | 2023 · 1 season | 2025 · 1 season |
| Sean Newcomb | RP | 2025 · 1 season | 2022 · 1 season |
| Eric Hosmer | 1B | 2022 · 1 season | 2023 · 1 season |
| Wade Miley | SP | 2015 · 1 season | 2022 · 1 season |
| Jonathan Herrera | 2B | 2014 · 1 season | 2015 · 1 season |
| Quintin Berry | OF | 2013 · 1 season | 2015 · 1 season |
| Brent Lillibridge | SS | 2012 · 1 season | 2013 · 1 season |
| Chris Carpenter | RP | 2012 · 1 season | 2011 · 1 season |
| Justin Germano | RP | 2012 · 1 season | 2012 · 1 season |
| Carlos Pena | 1B | 2006 · 1 season | 2011 · 1 season |
| David Aardsma | RP | 2008 · 1 season | 2006 · 1 season |
| Jermaine Van Buren | RP | 2006 · 1 season | 2005 · 1 season |
| Damian Jackson | CF | 2003 · 1 season | 2004 · 1 season |
| Jimmy Anderson | RP | 2004 · 1 season | 2004 · 1 season |
| Chris Stynes | 3B | 2001 · 1 season | 2002 · 1 season |
| Pat Mahomes | RP | 1997 · 1 season | 2002 · 1 season |
| Shane Andrews | 3B | 2002 · 1 season | 2000 · 1 season |
| Jeff Fassero | RP | 2000 · 1 season | 2001 · 1 season |
| Matt Stairs | 1B | 1995 · 1 season | 2001 · 1 season |
| Gary Gaetti | DH | 2000 · 1 season | 1999 · 1 season |
| Terry Shumpert | DH | 1995 · 1 season | 1996 · 1 season |
| Doug Bird | RP | 1983 · 1 season | 1982 · 1 season |
| Dave Rader | C | 1980 · 1 season | 1978 · 1 season |
| Mike O'Berry | C | 1979 · 1 season | 1980 · 1 season |
| Terry Hughes | — | 1974 · 1 season | 1970 · 1 season |
| Lee Thomas | — | 1965 · 1 season | 1967 · 1 season |
| Jack Spring | P | 1957 · 1 season | 1964 · 1 season |
| Ken Aspromonte | — | 1957 · 1 season | 1963 · 1 season |
| Al Schroll | P | 1958 · 1 season | 1960 · 1 season |
| Grady Hatton | — | 1955 · 1 season | 1960 · 1 season |
| Dick Littlefield | P | 1950 · 1 season | 1957 · 1 season |
| Dolph Camilli | — | 1945 · 1 season | 1933 · 1 season |
| Jim Brillheart | P | 1931 · 1 season | 1927 · 1 season |
| Jimmy Cooney | — | 1917 · 1 season | 1926 · 1 season |
| Marty Krug | — | 1912 · 1 season | 1922 · 1 season |
| Herb Hunter | — | 1920 · 1 season | 1917 · 1 season |
| Harry Wolter | — | 1909 · 1 season | 1917 · 1 season |
| Jack Hayden | — | 1906 · 1 season | 1908 · 1 season |
| Aleck Smith | — | 1903 · 1 season | 1904 · 1 season |
| Larry McLean | — | 1901 · 1 season | 1903 · 1 season |
| Frank Morrissey | P | 1901 · 1 season | 1902 · 1 season |
Regular season, under every name each club has played as. A season split by a trade counts for both clubs where the game logs reach it (NBA from 1993-94, NFL 1994, NHL 1996, MLB 2001). Longest stay with the two first.