In the 1898-99 season the Association assumed direct control of the senior competition rather than allowing the clubs to run the competition themselves, as had been the case for the previous three seasons. Five teams entered the senior competition but unfortunately Singleton withdrew early in the season. The competition was eventually won by Albion which finished undefeated.
Leon Moore had an outstanding season with the Pearl Club. He scored 951 runs for the season at an average of 118.8 and his aggregate included four centuries and a double century (214 n.o. vs Morpeth).
Wally McGlinchey left the district to go to Queensland to take up a 12 month position as coach of the State's National Cricket Union. During that time he played with the Zillmere CC and was reported as having "a very successful season with bat and ball". The Brisbane Courier hailed him as "without doubt the best all-round cricketer in Queensland".
Another district player, Bob Lindsay, who had already begun to make a name for himself was given high praise by Australian Test player Frank Iredale. He described Lindsay as "a fine batsman" who has "every promise of developing into a really good cricketer ... he has all the essentials of a good batsman and has, moreover, what is a strong characteristic in him. absolute fearlessness."
The season saw the formation of another Association - the Maitland District Junior Cricket Association. This was aimed at catering for the smaller clubs in the district that had a number of junior players. While it was not a "break-away organisation" it did weaken the numerical strength of the senior Association.
The fifth Annual General Report of the HRDCA was rather depressing. It stated "both from a cricketing point of view, as well as from a financial point of view, the past season cannot be regarded as a successful one". Apart from the withdrawal of Singleton from the senior competition, there had been several disputes in the junior competition "which tended to militate against the success and popularity of the competition matches". Many of the clubs had also neglected to forward score- sheet returns of matches.
On the financial side the Association was reported as being "in a deplorable financial state" with a large , deficit of £6.12.2. Even President Percy Waddy seemed to have lost some of his enthusiasm. In reluctantly accepting nomination for another term he deplored the lack of quorums at Association committee meetings and admitted he had "begun to lose heart" with the "lack of support from the public".