1960/1961

1^st round

Hartlepool Athletic II v Hartlepool O.B. II

Horden II v West Hartlepool G.S.O.B.

West Hartlepool T.D.S.O.B. v Hartlepool Rovers II

Hartlepool B.B.O.B. v West Hartlepool II

Semi finals

Hartlepool Athletic II v Horden

Hartlepool Rovers II v West Hartlepool II

Final

West Hartlepool II v Hartlepool Athletic II

Played at New Friarage, 12/04/1961

1961/1962

Preliminary round

Hartlepool Athletic II v West Hartlepool G.S.O.B.

West Hartlepool II v Hartlepool B.B.O.B.

West Hartlepool T.D.S.O.B. v Billingham II

1^st round

Horden v Hartlepool Rovers II

Stockton/Billingham T.C. v Hartlepool Athletic II

West Hartlepool II v Stockton II

Hartlepool O.B. II  3  West Hartlepool T.D.S.O.B.  17

Semi finals

Hartlepool Rovers II v Hartlepool Athletic II

West Hartlepool II  21  West Hartlepool T.D.S.O.B.  11

Final

West Hartlepool II  11  Hartlepool Rovers II  3

Played at New Friarage, 26/04/1962

1962/1963

Semi finals

Hartlepool Rovers II lost to West Hartlepool on Grayfields.

Hartlepool Athletic II lost to West Hartlepool T.D.S.O.B. on the Trading Estate

Played on 23/04/1963

Final

West Hartlepool II  28  West Hartlepool  6

Played at New Friarage 30/04/1963

1963/1964

1^st round

 Stockton/Billingham T.C. v Hartlepool Athletic II (both withdrew)

West Hartlepool T.D.S.O.B.  3  West Hartlepool II  15

Hartlepool B.B.O.B.  13  Hartlepool Rovers II  23

West Hartlepool G.S.O.B. v Hartlepool O.B. II

Semi finals

The 1^st round tie played on 23/04/1964 counted as a semi

Hartlepool Rovers II  10  West Hartlepool G.S.O.B.  3  (30/04/1964)

Finalists

Hartlepool Rovers II v West Hartlepool II

If a final was played it could only be on 2^nd May 1964.

1964/1965

Under County re-organisation the South Durham District Junior Union was disbanded and the duties split among various County sub committees. No provision was made for the Pyman Cup and it was not played for during this season. The Hartlepool & District Committee was formed in December 1965 and the Pyman Cup and West Shield restarted.

1965/1966

1^st round

Hartlepool B.B.O.B.  0  West Hartlepool T.D.S.O.B.  54

Hartlepool Rovers II walked over v West Hartlepool G.S.O.B.

West Hartlepool II walked over v Hartlepool Athletic II

Horden II  0  Hartlepool O.B. II  9

Semi finals

Hartlepool Rovers II  27  Hartlepool O.B. II  0

West Hartlepool II  3  West Hartlepool T.D.S.O.B.  19

Final

Hartlepool Rovers II  22  West Hartlepool T.D.S.O.B.  0

Played at Grayfields

1966/1967

1^st round

West Hartlepool T.D.S.O.B.  10  Hartlepool Rovers  3

Horden II  0  West Hartlepool II  37

Hartlepool O.B. II & Hartlepool B.B.O.B. byes

Semi finals

West Hartlepool T.D.S.O.B.  19  Hartlepool O.B. II  0

West Hartlepool II   15  Hartlepool B.B.O.B.  0

Final

West Hartlepool T.D.S.O.B.  13  West Hartlepool II  8

Played at New Friarage

1967/1968

1^st round

West Hartlepool II beat Hartlepool Athletic II

Hartlepool B.B.O.B. v Hartlepool O.B. II

West Hartlepool G.S.O.B.  6  Horden II  15

Hartlepool Rovers II conceded to West Hartlepool T.D.S.O.B.

Semi finals

West Hartlepool II  3  West Hartlepool T.D.S.O.B.  8

Horden v ?

Final tie

Horden II  12  West Hartlepool T.D.S.O.B.  6

Played at the King George V Field

1968/1969

1^st round

Hartlepool B.B.O.B. v Hartlepool O.B. II

Horden II  9  West Hartlepool T.D.S.O.B.  22

Hartlepool Athletic II  6  West Hartlepool G.S.O.B. 9

Hartlepool Rovers II  6  West Hartlepool II  8

Semi finals

West Hartlepool G.S.O.B.  3  Hartlepool B.B.O.B.  6

West Hartlepool T.D.S.O.B.  0  West Hartlepool  3

Final

West Hartlepool II  12  Hartlepool B.B.O.B.  9

After extra time. Played at New Friarage

1969/1970

1^st round

Hartlepool Rovers II  14  West Hartlepool II  8

West Hartlepool G.S.O.B.  0  Hartlepool O.B. II  14

West Hartlepool T.D.S.O.B.  12  Hartlepool B.B.O.B.  14

Hartlepool Athletic II withdrew v Horden II

Semi finals

Hartlepool Rovers II  31  Hartlepool B.B.O.B.  11

Horden II  3  Hartlepool O.B. II  32

Final

Hartlepool Rovers  30  Hartlepool O.B. II  6

Played at New Friarage