| Year | Date | Opponent | Us | Them | Result | W | L | T | OT | Where | Location | Field | Coach | Notes |
| 1921 | 12/2 | Pineville | 0 | 27 | L | 1 | Home | Middlesboro | East End Park | James Hupp | ||||
| 1922 | 11/30 | Pineville | 7 | 41 | L | 1 | Away | Pineville | R. F. Porter | |||||
| 1923 | 11/29 | Pineville | 0 | 24 | L | 1 | Away | Pineville | John Kilpatrick | |||||
| 1924 | 11/27 | Pineville | 0 | 14 | L | 1 | Home | Middlesboro | East End Park | John Kilpatrick | ||||
| 1930 | 11/21 | Pineville | 25 | 0 | W | 1 | Home | Middlesboro | East End Park | Case Thomasson | ||||
| 1931 | 11/21 | Pineville | 0 | 0 | T | 1 | Away | Pineville | Samuels Field | Case Thomasson | ||||
| 1932 | 11/18 | Pineville | 28 | 0 | W | 1 | Home | Middlesboro | East End Park | Case Thomasson | ||||
| 1933 | 11/25 | Pineville | 0 | 0 | T | 1 | Away | Pineville | Case Thomasson | |||||
| 1934 | 11/23 | Pineville | 33 | 0 | W | 1 | Home | Middlesboro | East End Park | Case Thomasson | ||||
| 1935 | 11/22 | Pineville | 0 | 0 | T | 1 | Away | Pineville | Case Thomasson | |||||
| 1936 | 11/21 | Pineville | 13 | 6 | W | 1 | Home | Middlesboro | East End Park | Case Thomasson | ||||
| 1937 | 11/20 | Pineville | 6 | 7 | L | 1 | Away | Pineville | Samuels Field | Case Thomasson | ||||
| 1938 | 11/18 | Pineville | 0 | 27 | L | 1 | Home | Middlesboro | East End Park | Case Thomasson | ||||
| 1939 | 11/24 | Pineville | 7 | 0 | W | 1 | Away | Pineville | Samuels Field | Case Thomasson | ||||
| 1940 | 11/15 | Pineville | 20 | 6 | W | 1 | Home | Middlesboro | Bradner Stadium | Case Thomasson | ||||
| 1941 | 11/14 | Pineville | 12 | 13 | L | 1 | Away | Pineville | Samuels Field | Case Thomasson | ||||
| 1942 | 11/13 | Pineville | 0 | 13 | L | 1 | Home | Middlesboro | Bradner Stadium | Case Thomasson | ||||
| 1943 | 10/1 | Pineville | 0 | 0 | T | 1 | Home | Middlesboro | Bradner Stadium | Case Thomasson | ||||
| 1943 | 11/12 | Pineville | 14 | 0 | W | 1 | Away | Pineville | Samuels Field | Case Thomasson | ||||
| 1944 | 11/10 | Pineville | 25 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Warren Campbell | ||||
| 1945 | 11/9 | Pineville | 20 | 0 | W | 1 | Away | Pineville | Samuels Field | Warren Campbell | ||||
| 1946 | 11/8 | Pineville | 21 | 6 | W | 1 | Home | Middlesboro | Bradner Stadium | Warren Campbell | ||||
| 1947 | 11/7 | Pineville | 19 | 21 | L | 1 | Away | Pineville | Samuels Field | Warren Campbell | ||||
| 1948 | 11/5 | Pineville | 47 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Warren Campbell | ||||
| 1949 | 11/4 | Pineville | 14 | 0 | W | 1 | Away | Pineville | Samuels Field | Warren Campbell | ||||
| 1950 | 11/3 | Pineville | 21 | 12 | W | 1 | Home | Middlesboro | Bradner Stadium | Warren Campbell | ||||
| 1951 | 11/2 | Pineville | 33 | 6 | W | 1 | Away | Pineville | Samuels Field | Warren Campbell | ||||
| 1952 | 10/31 | Pineville | 54 | 7 | W | 1 | Home | Middlesboro | Bradner Stadium | Warren Campbell | ||||
| 1953 | 10/30 | Pineville | 0 | 7 | L | 1 | Away | Pineville | Samuels Field | Warren Campbell | ||||
| 1954 | 10/29 | Pineville | 0 | 80 | L | 1 | Home | Middlesboro | Bradner Stadium | Warren Campbell | ||||
| 1955 | 10/28 | Pineville | 6 | 13 | L | 1 | Away | Pineville | Samuels Field | Moody Taylor | ||||
| 1956 | 10/26 | Pineville | 33 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Walt Green | ||||
| 1957 | 9/13 | Pineville | 27 | 12 | W | 1 | Away | Pineville | Samuels Field | Dave Hurst | ||||
| 1958 | 9/12 | Pineville | 27 | 6 | W | 1 | Home | Middlesboro | Bradner Stadium | Dave Hurst | ||||
| 1959 | 9/11 | Pineville | 25 | 7 | W | 1 | Away | Pineville | Samuels Field | Dave Hurst | ||||
| 1960 | 9/9 | Pineville | 13 | 6 | W | 1 | Home | Middlesboro | Bradner Stadium | Dave Hurst | ||||
| 1961 | 9/8 | Pineville | 0 | 16 | L | 1 | Away | Pineville | Samuels Field | Dave Hurst | ||||
| 1962 | 9/7 | Pineville | 12 | 7 | W | 1 | Home | Middlesboro | Bradner Stadium | Dave Hurst | ||||
| 1963 | 9/6 | Pineville | 7 | 7 | T | 1 | Away | Pineville | Samuels Field | Walt Green | ||||
| 1964 | 10/30 | Pineville | 59 | 7 | W | 1 | Away | Pineville | Samuels Field | Walt Green | ||||
| 1965 | 10/29 | Pineville | 34 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Walt Green | ||||
| 1966 | 10/28 | Pineville | 6 | 25 | L | 1 | Away | Pineville | Samuels Field | Walt Green | ||||
| 1967 | 10/27 | Pineville | 7 | 20 | L | 1 | Home | Middlesboro | Bradner Stadium | Walt Green | ||||
| 1968 | 11/1 | Pineville | 27 | 12 | W | 1 | Away | Pineville | Samuels Field | Bill Criscillis | ||||
| 1969 | 10/30 | Pineville | 0 | 30 | L | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | ||||
| 1970 | 10/30 | Pineville | 21 | 8 | W | 1 | Away | Pineville | Samuels Field | Tom Stapleton | ||||
| 1971 | 10/29 | Pineville | 20 | 8 | W | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | ||||
| 1972 | 10/27 | Pineville | 34 | 0 | W | 1 | Away | Pineville | Samuels Field | Tom Stapleton | ||||
| 1973 | 10/26 | Pineville | 2 | 6 | L | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | ||||
| 1974 | 11/1 | Pineville | 53 | 6 | W | 1 | Away | Pineville | Samuels Field | Tom Stapleton | ||||
| 1975 | 10/30 | Pineville | 39 | 20 | W | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | ||||
| 1976 | 10/29 | Pineville | 38 | 8 | W | 1 | Away | Pineville | Samuels Field | Tom Stapleton | ||||
| 1977 | 10/28 | Pineville | 20 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | ||||
| 1978 | 10/27 | Pineville | 41 | 14 | W | 1 | Away | Pineville | Samuels Field | Tom Stapleton | ||||
| 1979 | 9/7 | Pineville | 9 | 8 | W | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | ||||
| 1980 | 10/24 | Pineville | 30 | 6 | W | 1 | Away | Pineville | Samuels Field | Tom Stapleton | ||||
| 1981 | 10/23 | Pineville | 34 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ed Vanhoose | ||||
| 1982 | 10/21 | Pineville | 56 | 34 | W | 1 | Away | Pineville | Samuels Field | Ed Vanhoose | ||||
| 1983 | 10/20 | Pineville | 41 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ed Vanhoose | ||||
| 1984 | 10/19 | Pineville | 14 | 20 | L | 1 | 1OT | Away | Pineville | Samuels Field | Ed Vanhoose | |||
| 1985 | 10/25 | Pineville | 3 | 10 | L | 1 | Home | Middlesboro | Bradner Stadium | Roscoe Perkins | ||||
| 1986 | 10/24 | Pineville | 34 | 20 | W | 1 | Away | Pineville | Samuels Field | Roscoe Perkins | ||||
| 1987 | 8/21 | Pineville | 15 | 14 | W | 1 | Home | Middlesboro | Bradner Stadium | Roscoe Perkins | ||||
| 1988 | 8/19 | Pineville | 13 | 7 | W | 1 | 4OT | Away | Pineville | Samuels Field | Roscoe Perkins | |||
| 1989 | 8/25 | Pineville | 7 | 34 | L | 1 | Home | Middlesboro | Bradner Stadium | Gary Barnett | ||||
| 1990 | 8/25 | Pineville | 12 | 7 | W | 1 | Away | Pineville | Samuels Field | Gary Barnett | ||||
| 1991 | 8/30 | Pineville | 22 | 8 | W | 1 | Home | Middlesboro | Bradner Stadium | Gary Barnett | ||||
| 1992 | 8/28 | Pineville | 38 | 26 | W | 1 | Away | Pineville | Samuels Field | Gary Barnett | ||||
| 1993 | 9/10 | Pineville | 34 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Gary Barnett | ||||
| 1994 | 9/9 | Pineville | 49 | 7 | W | 1 | Away | Pineville | Samuels Field | Ken Roark | ||||
| 1995 | 9/15 | Pineville | 54 | 24 | W | 1 | Away | Pineville | Samuels Field | Ken Roark | ||||
| 1996 | 9/20 | Pineville | 41 | 28 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | ||||
| 1997 | 10/30 | Pineville | 41 | 0 | W | 1 | Away | Pineville | Samuels Field | Ken Roark | ||||
| 1998 | 10/29 | Pineville | 58 | 7 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | ||||
| 1999 | 9/24 | Pineville | 45 | 29 | W | 1 | Away | Pineville | Samuels Field | Ken Roark | ||||
| 2000 | 9/22 | Pineville | 49 | 18 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | ||||
| 2001 | 9/15 | Pineville | 39 | 12 | W | 1 | Away | Pineville | Samuels Field | Ken Roark | ||||
| 2002 | 9/20 | Pineville | 46 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | ||||
| 2003 | 9/5 | Pineville | 36 | 6 | W | 1 | Away | Pineville | Samuels Field | Ken Roark | ||||
| 2004 | 9/3 | Pineville | 27 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | ||||
| 2005 | 9/2 | Pineville | 40 | 13 | W | 1 | Away | Pineville | Samuels Field | Ken Roark | ||||
| 2006 | 9/1 | Pineville | 60 | 7 | W | 1 | Away | Pineville | Samuels Field | Ken Roark | ||||
| 2013 | 9/6 | Pineville | 42 | 20 | W | 1 | Home | Middlesboro | Bradner Stadium | Randy Frazier | ||||
| 2014 | 9/5 | Pineville | 43 | 0 | W | 1 | Away | Pineville | Samuels Field | Zach Massengill | ||||
| 2015 | 9/4 | Pineville | 31 | 40 | L | 1 | Home | Middlesboro | Bradner Stadium | Zach Massengill | ||||
| 2016 | 9/2 | Pineville | 23 | 16 | W | 1 | Away | Pineville | Samuels Field | Zach Massengill | ||||
| 2017 | 9/15 | Pineville | 46 | 20 | W | 1 | Home | Middlesboro | Bradner Stadium | Zach Massengill | ||||
| 2018 | 9/14 | Pineville | 24 | 30 | L | 1 | Away | Pineville | Samuels Field | Zach Massengill | ||||
| 2019 | 9/20 | Pineville | 20 | 19 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | ||||
| 2020 | 9/18 | Pineville | 35 | 20 | W | 1 | Away | Pineville | Samuels Field | Larry French | ||||
| 2022 | 10/28 | Pineville | 41 | 38 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | ||||
| 2023 | 10/6 | Pineville | 47 | 6 | W | 1 | Away | Pineville | Samuels Field | Larry French | ||||
| 2024 | 10/11 | Pineville | 36 | 14 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | ||||
| 2025 | 10/10 | Pineville | 50 | 0 | W | 1 | Away | Pineville | Samuels Field | Larry French | ||||
| 2,355 | 1,123 | 67 | 22 | 5 | .739 | |||||||||
| 25.05 | 11.95 | 13.11 |