Chepstow Cricket Club was formed in 1838, and they played their inaugural match against Monmouth C.C. on August 25th. The club became successful enough to secure fixtures in the Bristol area, although this required a crossing of the Severn by ferry! Their fixture list expanded during the 1850's following the opening of the Gloucester to Cardiff railway line, which passed through Chepstow.

By June 1881 the club's fixture list included Thornbury C.C., and a large crowd was attracted to the home fixture as the Thornbury side included W.G.Grace. But the Doctor was dismissed for a duck, caught behind for a duck from his second ball. His dismissal resulted in a variety of reactions - cheers came from some of the locals, whilst others voiced their disapproval having paid up to five shillings in admission money. But perhaps the most startling came from the Doctor himself, who threw down his bat in temper, left the ground and caught the next train home to Bristol!

During these early years the club played in the spacious grounds of Piercefield Park, the home of the Clay family, to the north of the town where the racecourse currently exists. Around the turn of the century, the cricket club moved to a ground called High Beech, and with the support of the Clay family, a pavilion was erected. The inter-war years saw mant members of the Clay family turn out for the club, including J.C.Clay, whilst Louis Stedman and Gordon Phillips, two of Monmouthshire's best amateurs, moved to Chepstow from Newport. The High Beech wicket became one of the best in the area, and quite fittingly the ground hosted Monmouthshire's Minor County fixtures between 1926 and 1930.

In 1939 the High Beech ground was ploughed up as part of the "Dig for Victory" campaig and Chepstow C.C. went temporarily out of existence. In 1956 they were resurrected after a meeting at the town's Beaufort Hotel, and following assistance from Chepstow Urban District Council, the club secured the Bulwark Sport and Social Club's ground in Mathern Ground, on the south-eastern side of the town. A lot of ground improvements and building work took place during the year, and in 1957 the ground was formally opened by a match involving a Glamorgan XI selected by J.C.Clay.

The county staged annual club and ground fixtures at Chepstow during the 1960's and in 1973 they played their inaugural Second Eleven fixture at the ground. The 1970's was an important decade for the Chepstow club as they entered the Gwent Pemier League in 1973, and as a result of their success in this competition, they also entered the Three Counties League in 1982. Although Glamorgan C.C.C. no longer play 2nd XI games at the Bulwark ground, there is still a link with the Chepstow club as Adrian Dale, the county's all-rounder was brought up in the town and played, together with his father, with great success for the club.