- 2027-04-02 in 5mo Middlesbrough at Portsmouth
- 2026-12-18 in 1mo Portsmouth at Middlesbrough
- 2026-04-11 6mo Portsmouth 1 at Middlesbrough 0 Jordan Williams ENG-PORT 75min yc
- 2025-10-04 1y Middlesbrough 0 at Portsmouth 1 Jordan Williams ENG-PORT 64min
- 2025-01-18 1y Middlesbrough 1 at Portsmouth 2 Matt Ritchie ENG-PORT 90min
- 2024-08-24 2y Portsmouth 2 at Middlesbrough 2
- 2012-03-03 14y Middlesbrough 3 at Portsmouth 1 Matthew Bates ENG-MIRM 90min 1g yc
- 2011-03-12 15y Middlesbrough 0 at Portsmouth 0
- 2010-10-02 16y Portsmouth 2 at Middlesbrough 2
- 2009-03-14 17y Portsmouth 1 at Middlesbrough 1
- 2008-09-13 18y Middlesbrough 1 at Portsmouth 2 Jermain Colin Defoe ENG-POVF 90min 2g yc
- 2008-05-03 18y Portsmouth 0 at Middlesbrough 2 Mark Schwarzer ENG-MIRM 90min
- 2007-12-29 18y Middlesbrough 1 at Portsmouth 0 Tuncay Şanlı ENG-MIRM 90min 1g
- 2007-01-30 19y Middlesbrough 0 at Portsmouth 0
- 2006-08-28 20y Portsmouth 4 at Middlesbrough 0 Nwankwo Christian Kanu ENG-POVF 83min 2g
- 2006-04-15 20y Middlesbrough 0 at Portsmouth 1 ENG-POVF 90min 1g
- 2005-10-15 21y Portsmouth 1 at Middlesbrough 1
- 2005-02-01 21y Middlesbrough 1 at Portsmouth 2 Yakubu Aiyegbeni ENG-POVF 90min 1g
- 2004-10-24 22y Portsmouth 1 at Middlesbrough 1
- 2004-05-15 22y Middlesbrough 1 at Portsmouth 5 Yakubu Aiyegbeni ENG-POVF 90min 4g
- 2003-12-06 22y Portsmouth 0 at Middlesbrough 0
- 1998-03-14 28y Middlesbrough 0 at Portsmouth 0
- 1997-11-05 28y Portsmouth 1 at Middlesbrough 1
- 1994-12-03 31y Portsmouth 0 at Middlesbrough 4
- 1994-10-23 32y Middlesbrough 0 at Portsmouth 0
- 1994-04-16 32y Portsmouth 2 at Middlesbrough 0
- 1993-11-02 32y Middlesbrough 0 at Portsmouth 2
- 1954-03-20 72y Portsmouth 2 at Middlesbrough 2
- 1953-05-02 73y Middlesbrough 4 at Portsmouth 1
- 1952-12-13 73y Portsmouth 2 at Middlesbrough 3
- 1952-03-01 74y Portsmouth 1 at Middlesbrough 2
- 1951-10-13 75y Middlesbrough 4 at Portsmouth 5
- 1950-12-16 75y Portsmouth 1 at Middlesbrough 3
- 1950-08-19 76y Middlesbrough 1 at Portsmouth 1
- 1949-12-31 76y Middlesbrough 1 at Portsmouth 1
- 1949-09-03 77y Portsmouth 5 at Middlesbrough 1
- 1948-09-15 78y Portsmouth 1 at Middlesbrough 1
- 1948-09-08 78y Middlesbrough 0 at Portsmouth 1
- 1948-04-14 78y Middlesbrough 1 at Portsmouth 6
- 1947-09-20 79y Portsmouth 2 at Middlesbrough 1
- 1947-03-29 79y Middlesbrough 1 at Portsmouth 3
- 1946-11-23 79y Portsmouth 3 at Middlesbrough 3
- 1939-03-29 87y Portsmouth 2 at Middlesbrough 8
- 1938-11-19 87y Middlesbrough 1 at Portsmouth 1
- 1938-01-26 88y Portsmouth 0 at Middlesbrough 0
- 1937-09-11 89y Middlesbrough 2 at Portsmouth 0
- 1937-01-02 89y Portsmouth 2 at Middlesbrough 2
- 1936-09-05 90y Middlesbrough 1 at Portsmouth 2
- 1935-12-28 90y Middlesbrough 0 at Portsmouth 1
- 1935-08-31 91y Portsmouth 2 at Middlesbrough 3