During the next four seasons local cricket was to fall further into the doldrums and the continued existence of the Association was to be called into Question.
In 1899-1900 the number of affiliated clubs dropped from 11 to 8. There were only four clubs remaining in the senior competition - Albion, Pearl, Morpeth and East Maitland. The junior badge competition had six teams with the names of the old established clubs of Branxton, Woodville and Lochinvar appearing for the first time in the Association's competition.
Country Week was revived and held in November 1899. Following the week's matches, four HRDCA players - L Moore, H Harden, R Norman and W Lipscomb - were selected to play for Northern District against a Metropolitan team in Maitland on Christmas and Boxing Day. Financially, however, Country Week was a failure - six months later the local Association received a "paltry cheque" for £1.14s. as its share of the profits.
In an effort to encourage the younger cricketers in the district the Association arranged a match on the Albion ground between HRDCA juniors and a team of Sydney "second juniors" from the NSW Junior Association. The match resulted in a win for the Sydney team by a few runs on the first innings.
The Annual Report for the season presented a very gloomy picture. It stated "the efforts of the Association to promote the welfare of cricket had met with little success" . there had been very little interest in senior cricket; public interest in cricket had generally declined; and the Association had liabilities amounting to £23. Foundation President, Mr Percy Waddy, also announced his retirement. The election of office- bearers was stood over for a further meeting - indication of the difficulty of getting nominees to serve on the Association.