Two new clubs - Raymond Terrace and Murmuring affiliated with the Association for the 1895-96 season and entered teams in the junior competition.
The electorate matches involving Singleton, East Maitland and West Maitland proved to be a failure. They were criticized during the season for depriving too many players of their Saturday cricket. For example, when West Maitland played East Maitland in one of these two day electorate matches the West Maitland team would be chosen from the Pearl and Albion clubs, while the East Maitland team would be chosen from the Morpeth and East Maitland clubs.
However, this would leave 22 other players without any cricket for two Saturdays. At the second Annual General Meeting in September 1896 the Association President, Percy Waddy, admitted "the Electorate cricket had been a failure". The Annual Report stated "contrary to expectations the change did not meet with any beneficial result from a cricket point of view, nor was it appreciated by the general public ... Your committee, now being of opinion, that the time is premature in this district for such a reform, advise discontinuance of same for the present". The recommendation was adopted without opposition.
To make matters worse during the second season the Association suffered a financial loss, largely as a result of the expenditure of sending players to Sydney for Country Week and a decline in public attendance at inter-district matches, where a gate entrance fee was charged. On a brighter note President PM Waddy announced he was prepared to donate five guineas for a trophy to be competed for in the junior competition in the coming 1896-97 season.