1950/1951

1^st round

Stockton II, Darlington G.S.O.B. II, West Hartlepool II

Hartlepool Athletic, Hartlepool Rovers II, Darlington R.A. II byes

Hartlepool O.B. II v Horden

Siemens, Hartlepool v Hartlepool B.B.O.B.

2^ND round

Stockton II v Darlington G.S.O.B. II (Stockton withdrew)

West Hartlepool II v Horden II

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

Hartlepool Rovers II v Darlington R.A. II

Semi finals

Darlington G.S.O.B. v Horden

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

Final Tie

Hartlepool Rovers II  6  Horden  0

21^st April 1951

1951/1952

Preliminary round

Hartlepool Rovers II  22  West Hartlepool  0

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

Hartlepool Athletic II scratched v Hartlepool O.B. II

Siemens scratched v Hartlepool B.B.O.B.

Darlington G.S.O.B. II and Darlington II scratched

Darlington R.A. bye

Billingham v Glaxo Labs

Old Dawsonians  8  Horden  6

2^nd round

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

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

Darlington R.A. bye

Glaxo Labs scratched against Old Dawsonians

Semi finals

Hartlepool Rovers II  22  Hartlepool O.B. II  0

Darlington R.A. lost to Old Dawsonians

Final

Finalists known by the end of the season. However, Old Dawsonians folded during the close season and Rovers II were awarded the trophy.

1952/1953

1^st round

Hartlepool Athletic II and Hartlepool B.B.O.B. bye

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

Hartlepool Rovers II v West Hartlepool II

Semi finals

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

Hartlepool O.B. II v ?

Clubs not fulfilling dates barred

Final

Hartlepool B.B.O.B.  9  Hartlepool O.B. II  0

King George V Field, 24^th April 1953.

1953/1954

1^st round

Hartlepool B.B.O.B. awarded tie v West Hartlepool G.S.O.B.

West Hartlepool T.D.S.O.B. withdrew v Horden

West Hartlepool II v Hartlepool O.B. II

Hartlepool Rovers II withdrew v Hartlepool Athletic

Hartlepool B.B.O.B. progressed, Horden withdrew

Hartlepool O.B. II v Hartlepool Athletic II

Final

Hartlepool Athletic II  6  Hartlepool B.B.O.B.  3

New Friarage 24  April, 1954

1954/1955

1^st round

Hartlepool O.B. II v Hartlepool Rovers II

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

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

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

Semi finals

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

West Hartlepool II v Hartlepool Athletic II

Final

West Hartlepool II 14 West Hartlepool G.S.O.B. 10

According to the Northern Daily Mail, the semi final was on Easter Monday, 11^th April 1955:

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

The following Saturday (16^th April) the finalists met in a friendly with G.S.O.B. winning 11-0 (?)

1955/1956

1^st round

Hartlepool Rovers II  61  West Hartlepool T.D.S.O.B.  0

Horden v Hartlepool B.B.O.B.

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

Hartlepool O.B. II v Hartlepool Athletic

Final

Hartlepool Rovers II  9  West Hartlepool II  6

Gryehound Sadium - 30 April, 1956.

1956/1957

1^st round

Horden v West Hartlepool II (West awarded tie)

Hartlepool Rovers II v Hartlepool O.B. II

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

Hartlepool B.B.O.B. v West Hartlepool G.S.O.B. (GSOB awarded tie)

Semi finals

West Hartlepool II  9  Hartlepool Rovers II  11

West Hartlepool T.D.S.O.B. v West Hartlepool G.S.O.B.

Played at Grayfields, 22^nd April 1957

Final

Hartlepool Rovers II  14  West Hartlepool G.S.O.B.  3

New Friarage 24 April, 1957

1957/1958

1^st round

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

Hartlepool Rovers II 3 West Hartlepool II 12

Hartlepool Athletic II v West Hartlepool G.S.O.B. (GSOB awarded tie)

Hartlepool O.B. II 16 Hartlepool B.B.O.B. 0

Semi finals

Horden v West Hartlepool II

West Hartlepool G.S.O.B.  0  Hartlepool O.B.  3

Final

West Hartlepool II  3  Hartlepool O.B.  0

New Friarage 26.4.1958

1958/1959

Preliminary round

Hartlepool Rovers II v Hartlepool O.B. II

1^st round

1. Hartlepool Rovers II v Durham Police (07/04/1959)
2. Horden II v West Hartlepool II
3. West Hartlepool T.D.S.O.B. v Hartlepool Athletic II
4. Hartlepool B.B.O.B. v West Hartlepool G.S.O.B.

Semi finals

? v Horden

? v West HartlepooL G.S.O.B.

Final

Horden  15  West Hartlepool G.S.O.B.  0

Played at the Greyhound Stadium, Clarence Road, 29/04/1959

1959/1960

Preliminary round

West Hartlepool T.D.S.O.B. v Police Cadets

1^st round

Hartlepool B.B.O.B. v Horden

Hartlepool O.B. II v Police Cadets

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

Hartlepool Rovers II v West Hartlepool II

Semi finals

Horden v ?

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

Final

Hartlepool Rovers II  29  Horden  6