Middlesbrough have played Chelsea 120 times in competitive football, winning 32, drawing 29 and losing 59, first meeting on 26 Dec 1907 and most recently on 23 Jan 2024. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 26 Dec 1907 | 1907–08 | First Division | A | Chelsea | 0–1 | ||
| 1 Jan 1908 | 1907–08 | First Division | H | Chelsea | 3–1 | ||
| 1 Jan 1909 | 1908–09 | First Division | H | Chelsea | 1–4 | ||
| 9 Apr 1909 | 1908–09 | First Division | A | Chelsea | 0–3 | ||
| 9 Oct 1909 | 1909–10 | First Division | H | Chelsea | 0–1 | ||
| 19 Feb 1910 | 1909–10 | First Division | A | Chelsea | 1–2 | ||
| 14 Dec 1912 | 1912–13 | First Division | A | Chelsea | 3–2 | ||
| 19 Apr 1913 | 1912–13 | First Division | H | Chelsea | 0–3 | ||
| 1 Nov 1913 | 1913–14 | First Division | A | Chelsea | 2–3 | ||
| 7 Mar 1914 | 1913–14 | First Division | H | Chelsea | 2–0 | ||
| 19 Sep 1914 | 1914–15 | First Division | H | Chelsea | 3–0 | ||
| 23 Jan 1915 | 1914–15 | First Division | A | Chelsea | 2–2 | ||
| 22 Nov 1919 | 1919–20 | First Division | H | Chelsea | 0–0 | ||
| 29 Nov 1919 | 1919–20 | First Division | A | Chelsea | 1–3 | ||
| 23 Apr 1921 | 1920–21 | First Division | H | Chelsea | 0–0 | ||
| 30 Apr 1921 | 1920–21 | First Division | A | Chelsea | 1–1 | ||
| 26 Dec 1921 | 1921–22 | First Division | H | Chelsea | 0–1 | ||
| 27 Dec 1921 | 1921–22 | First Division | A | Chelsea | 1–1 | ||
| 9 Sep 1922 | 1922–23 | First Division | A | Chelsea | 1–1 | ||
| 16 Sep 1922 | 1922–23 | First Division | H | Chelsea | 2–1 | ||
| 17 Nov 1923 | 1923–24 | First Division | H | Chelsea | 2–0 | ||
| 24 Nov 1923 | 1923–24 | First Division | A | Chelsea | 0–2 | ||
| 13 Dec 1924 | 1924–25 | Second Division | A | Chelsea | 0–2 | ||
| 18 Apr 1925 | 1924–25 | Second Division | H | Chelsea | 1–1 | ||
| 12 Dec 1925 | 1925–26 | Second Division | H | Chelsea | 1–2 | Owen Williams 65 | |
| 24 Apr 1926 | 1925–26 | Second Division | A | Chelsea | 1–0 | Jimmy McClelland 56 | |
| 28 Aug 1926 | 1926–27 | Second Division | A | Chelsea | 0–3 | ||
| 15 Jan 1927 | 1926–27 | Second Division | H | Chelsea | 0–0 | ||
| 6 Sep 1928 | 1928–29 | Second Division | A | Chelsea | 0–2 | ||
| 19 Jan 1929 | 1928–29 | Second Division | H | Chelsea | 4–5 | Owen Williams 10, Billy Pease 50, Billy Pease 89, George Camsell 82 | |
| 4 Oct 1930 | 1930–31 | First Division | A | Chelsea | 0–4 | ||
| 7 Feb 1931 | 1930–31 | First Division | H | Chelsea | 2–2 | ||
| 29 Aug 1931 | 1931–32 | First Division | H | Chelsea | 0–2 | ||
| 2 Jan 1932 | 1931–32 | First Division | A | Chelsea | 0–4 | ||
| 8 Oct 1932 | 1932–33 | First Division | A | Chelsea | 1–2 | ||
| 1 Mar 1933 | 1932–33 | First Division | H | Chelsea | 2–1 | ||
| 14 Oct 1933 | 1933–34 | First Division | A | Chelsea | 3–2 | ||
| 24 Feb 1934 | 1933–34 | First Division | H | Chelsea | 2–2 | ||
| 22 Dec 1934 | 1934–35 | First Division | A | Chelsea | 1–2 | ||
| 4 May 1935 | 1934–35 | First Division | H | Chelsea | 2–2 | ||
| 9 Nov 1935 | 1935–36 | First Division | A | Chelsea | 1–2 | ||
| 4 Mar 1936 | 1935–36 | First Division | H | Chelsea | 4–1 | ||
| 12 Sep 1936 | 1936–37 | First Division | H | Chelsea | 2–0 | ||
| 9 Jan 1937 | 1936–37 | First Division | A | Chelsea | 0–1 | ||
| 18 Sep 1937 | 1937–38 | First Division | H | Chelsea | 4–3 | ||
| 29 Jan 1938 | 1937–38 | First Division | A | Chelsea | 1–0 | ||
| 10 Sep 1938 | 1938–39 | First Division | H | Chelsea | 1–1 | ||
| 14 Jan 1939 | 1938–39 | First Division | A | Chelsea | 2–4 | ||
| 5 Oct 1946 | 1946–47 | First Division | H | Chelsea | 3–2 | ||
| 10 May 1947 | 1946–47 | First Division | A | Chelsea | 0–2 | ||
| 18 Oct 1947 | 1947–48 | First Division | A | Chelsea | 2–4 | ||
| 6 Mar 1948 | 1947–48 | First Division | H | Chelsea | 0–0 | ||
| 21 Aug 1948 | 1948–49 | First Division | A | Chelsea | 0–1 | ||
| 18 Dec 1948 | 1948–49 | First Division | H | Chelsea | 1–1 | ||
| 26 Nov 1949 | 1949–50 | First Division | H | Chelsea | 2–1 | ||
| 29 Mar 1950 | 1949–50 | First Division | A | Chelsea | 1–2 | ||
| 26 Aug 1950 | 1950–51 | First Division | H | Chelsea | 3–0 | ||
| 23 Dec 1950 | 1950–51 | First Division | A | Chelsea | 1–1 | ||
| 6 Oct 1951 | 1951–52 | First Division | H | Chelsea | 0–0 | ||
| 16 Feb 1952 | 1951–52 | First Division | A | Chelsea | 0–5 | ||
| 29 Nov 1952 | 1952–53 | First Division | H | Chelsea | 4–0 | ||
| 18 Apr 1953 | 1952–53 | First Division | A | Chelsea | 1–1 | ||
| 17 Oct 1953 | 1953–54 | First Division | A | Chelsea | 1–1 | ||
| 6 Mar 1954 | 1953–54 | First Division | H | Chelsea | 3–3 | ||
| 20 Oct 1962 | 1962–63 | Second Division | A | Chelsea | 2–3 | ||
| 9 Mar 1963 | 1962–63 | Second Division | H | Chelsea | 1–0 | ||
| 13 Sep 1967 | 1967–68 | League Cup | H | Chelsea | 2–1 | ||
| 7 Oct 1970 | 1970–71 | League Cup | A | Chelsea | 2–3 | ||
| 7 Sep 1974 | 1974–75 | First Division | H | Chelsea | 1–1 | ||
| 22 Mar 1975 | 1974–75 | First Division | A | Chelsea | 2–1 | ||
| 15 Oct 1977 | 1977–78 | First Division | A | Chelsea | 0–0 | ||
| 4 Apr 1978 | 1977–78 | First Division | H | Chelsea | 2–0 | ||
| 16 Dec 1978 | 1978–79 | First Division | H | Chelsea | 7–2 | ||
| 21 Apr 1979 | 1978–79 | First Division | A | Chelsea | 1–2 | ||
| 11 Dec 1982 | 1982–83 | Second Division | H | Chelsea | 3–1 | ||
| 14 May 1983 | 1982–83 | Second Division | A | Chelsea | 0–0 | ||
| 24 Sep 1983 | 1983–84 | Second Division | A | Chelsea | 0–0 | ||
| 2 Jan 1984 | 1983–84 | Second Division | H | Chelsea | 2–1 | Gary Hamilton 39, David Currie 87 | |
| 15 May 1988 | 1987–88 | Play-offs | A | Chelsea | 0–1 | 40,550 | |
| 25 May 1988 | 1987–88 | Play-offs | H | Chelsea | 2–0 | Trevor Senior 30, Bernie Slaven 81 | 25,531 |
| 28 May 1988 | 1987–88 | Play-offs | A | Chelsea | 0–1 | ||
| 25 Mar 1990 | 1989–90 | Full Members Cup | N | Chelsea | 0–1 | 76,369 | |
| 11 Dec 1992 | 1992–93 | Premier League | H | Chelsea | 0–0 | 15,599 | |
| 13 Jan 1993 | 1992–93 | FA Cup | H | Chelsea | 2–1 | ||
| 3 Apr 1993 | 1992–93 | Premier League | A | Chelsea | 0–4 | 13,043 | |
| 26 Aug 1995 | 1995–96 | Premier League | H | Chelsea | 2–0 | Craig Hignett, Jan Åge Fjørtoft | 28,286 |
| 4 Feb 1996 | 1995–96 | Premier League | A | Chelsea | 0–5 | 21,060 | |
| 21 Aug 1996 | 1996–97 | Premier League | A | Chelsea | 0–1 | 28,272 | |
| 22 Mar 1997 | 1996–97 | Premier League | H | Chelsea | 1–0 | Juninho | 29,811 |
| 17 May 1997 | 1996–97 | FA Cup | N | Chelsea | 0–2 | 79,160 | |
| 29 Mar 1998 | 1997–98 | League Cup | N | Chelsea | 0–2 | 77,698 | |
| 26 Sep 1998 | 1998–99 | Premier League | A | Chelsea | 0–2 | 34,811 | |
| 14 Apr 1999 | 1998–99 | Premier League | H | Chelsea | 0–0 | 34,406 | |
| 25 Sep 1999 | 1999–00 | Premier League | H | Chelsea | 0–1 | 34,183 | |
| 22 Apr 2000 | 1999–00 | Premier League | A | Chelsea | 1–1 | Hamilton Ricard | 34,467 |
| 16 Dec 2000 | 2000–01 | Premier League | H | Chelsea | 1–0 | Dean Gordon | 29,422 |
| 31 Mar 2001 | 2000–01 | Premier League | A | Chelsea | 1–2 | Dean Windass | 34,933 |
| 23 Sep 2001 | 2001–02 | Premier League | A | Chelsea | 2–2 | Robbie Stockdale 61, Alen Bokšić 90 | 36,767 |
| 27 Apr 2002 | 2001–02 | Premier League | H | Chelsea | 0–2 | 28,686 | |
| 16 Nov 2002 | 2002–03 | Premier League | A | Chelsea | 0–1 | 39,064 | |
| 14 Dec 2002 | 2002–03 | Premier League | H | Chelsea | 1–1 | Geremi 32 | 29,160 |
| 4 Jan 2003 | 2002–03 | FA Cup | A | Chelsea | 0–1 | 29,796 | |
| 5 Oct 2003 | 2003–04 | Premier League | H | Chelsea | 1–2 | Szilárd Németh 46 | 29,170 |
| 10 Apr 2004 | 2003–04 | Premier League | A | Chelsea | 0–0 | 40,873 | |
| 25 Sep 2004 | 2004–05 | Premier League | H | Chelsea | 0–1 | 32,341 | |
| 4 Jan 2005 | 2004–05 | Premier League | A | Chelsea | 0–2 | 40,982 | |
| 3 Dec 2005 | 2005–06 | Premier League | A | Chelsea | 0–1 | 41,666 | |
| 11 Feb 2006 | 2005–06 | Premier League | H | Chelsea | 3–0 | Fábio Rochemback 2, Stewart Downing 45+2, Yakubu 68 | 31,037 |
| 23 Aug 2006 | 2006–07 | Premier League | H | Chelsea | 2–1 | Emanuel Pogatetz 80, Mark Viduka 90 | 29,198 |
| 10 Feb 2007 | 2006–07 | Premier League | A | Chelsea | 0–3 | 41,699 | |
| 20 Oct 2007 | 2007–08 | Premier League | H | Chelsea | 0–2 | 27,699 | |
| 30 Mar 2008 | 2007–08 | Premier League | A | Chelsea | 0–1 | 39,993 | |
| 18 Oct 2008 | 2008–09 | Premier League | H | Chelsea | 0–5 | 29,221 | |
| 28 Jan 2009 | 2008–09 | Premier League | A | Chelsea | 0–2 | 40,280 | |
| 27 Feb 2013 | 2012–13 | FA Cup | H | Chelsea | 0–2 | 27,856 | |
| 20 Nov 2016 | 2016–17 | Premier League | H | Chelsea | 0–1 | 32,704 | |
| 8 May 2017 | 2016–17 | Premier League | A | Chelsea | 0–3 | 41,500 | |
| 19 Mar 2022 | 2021–22 | FA Cup | H | Chelsea | 0–2 | 31,422 | |
| 9 Jan 2024 | 2023–24 | League Cup | H | Chelsea | 1–0 | Hayden Hackney 37 | 32,097 |
| 23 Jan 2024 | 2023–24 | League Cup | A | Chelsea | 1–6 | Morgan Rogers 88 | 37,754 |
See also: the Chelsea archive and Chelsea v Middlesbrough.
All Middlesbrough head-to-head records · Middlesbrough season by season