Harold English Pyman (1876 – 1917), was a West Hartlepool ship-owner, and a rugby referee, later Secretary of the Referees Society and famed for being a martinet on the field. In 1904 he presented a trophy for competition among the junior clubs in the Hartlepool area. Only clubs based within the Hartlepool and District area were eligible to compete for the trophy, and the ‘area’ in question was defined as being within 8 miles of the Heugh Lighthouse on the Headland. Originally the competition was on a League basis only. 

The Competition, quickly nicknamed The Pyman League, was a success among Junior Clubs and lower teams from the Senior Cubs.  After a few seasons, the League Committee (with Mr Claude Harper as its first Secretary) commenced a programme of games between the Pyman League XV and sides such as the Champion Club of the season, Hartlepool Rovers, and the Tyneside League.  

Following the restart of matters Rugby post War in 1920, the Competition was revived as part of the Hartlepool & District Union remit that year and the following six seasons saw the League at its greatest popularity extending to two divisions and talk of a third being run.

The heady days of the early 20s were not last and with a decline in popularity was followed by the League being suspended in 1926 by the Durham County RFU due to allegations of irregularities over the movement of players and an honorarium paid to the Secretary. Since then, the Pyman Cup has been played for on a knock-out competition basis with mid-week matches proving popular. In recent seasons, the Cup has been run as a 20 minutes each way /15 a side competition, however in 2023, which marks the 120th Anniversary of the Cup's foundation, it reverted to its traditional knockout format, 80 minutes each way.