The Victorian Soccer Federation’s intended plans to decrease the number of teams in the State League to ten failed in 1990, fortunately for Ringwood. In fact, with the return of dumped NSL side Heidelberg to the league it blew out to 18 clubs, and the VSF was forced to introduce double header weekends. This arrangement was a disaster for Ringwood who, despite the appointment of coach Kaz Kulak following the retirement of Hans Petersen, lacked the talent and depth to compete with the bigger clubs under such a heavy workload. The club replaced Kulak with John Corvan mid-season, but still failed to avoid relegation, finishing in 16th spot and relegated as the VSF finally managed to reduce the number of teams for season 1991.

The season break resulted in the loss of many first team regulars and, when 1991 began, Ringwood was left with a mere skeleton of it’s 1990 team – most of the surviving remnant being from the previous year’s reserve team. With soccer feeling the financial pinch the club was unable to recruit as freely as in the past but, despite this, began its campaign in some style. Unfortunately things began to fall apart and recently appointed coach Harry Chalkitis was axed, to be replaced by (who else) Sjel de Bruyckere. The club eventually struggled to a league position of tenth, and lost their second round Dockerty Cup encounter against Springvale United on penalties after a 1-1 extra time finish.

1992 almost became a disaster as key players left the club, forcing the coach to rely on a very young and inexperienced team to avoid relegation. In the end keeper Brian Vasey’s weekly brilliance proved to be the difference as the club finished a humble twelfth. Looking to be more competitive in 1993 the club was boosted by the return of goalscorer John Nyholt, as well as the arrival of nine other new faces. In a remarkable turn of events the previous season’s star performer Brian Vasey lost his position to newly arrived keeper Martin Posar after becoming embroiled in a feud with a member of the committee. The season proved to be a mixed bag of results, with a poor run of home form leaving the team in eighth place at season’s end.

Season 94 began with more uncertainty as John Davie was appointed as coach in place of Groenewald. An influx of new signings ensured a good season start but, by mid-season, the side was falling apart and Davie was released by the club who turned back to Groenewald. With the departure of striker John Nyholt (who opted to try his luck overseas) the club struggled to score consistently, and ended up slumping to rock bottom on the table. Further sadness was experienced at the club with the passing of founder John van Hoboken, who died at the age of 85. Season 95 began no better, with the club in the Second Division for the first time since 1956. Michael Sinclair was given the mammoth job of coaching the side but, with a paper thin group of players to work with, his job was always going to be extremely difficult. Even the introduction of some very experienced players to the club was not enough for Ringwood to avoid relegation for the second year running.

The arrival of Millissa Fischer-Massa in 1996 signalled a turnaround in the fortunes of Ringwood City. Having no small finance at her disposal, she committed herself to reviving the grand reputation of the club. Many new players were recruited – most notably striker Michael Michalakopoulos – and former Wilhelmina keeper John Kennedy was appointed first team coach. Michalakopoulos’ 35 goals in 25 games were to prove a key factor in Ringwood’s excellent campaign, with the club finishing agonisingly close behind champions Frankston Strikers. Second place was seen as a failure by Fischer-Massa, and Kennedy was replaced by Shaun Parton as coach for season 97. His brief was simple – win the title. The loss of Michalakopoulos to Premier League side Altona Magic was an unpleasant early season setback, but he returned in round seven to add to Ringwood City that spark which they had missed, and the club stepped up a gear to claim its first League championship in 30 years.

State League Division 3 Runners-up 1996

Ringwood’s success was to be short lived. Parton’s pre-season departure after a pay dispute paved the way for a Kaz Kulak coaching return, but it was a cash flow problem of benefactor Fischer-Massa that proved the most damaging event of the season, with Fischer-Massa opting to remove here financial interest when the board refused to bankroll the team temporarily. Without her and her money Michalakopoulos and many of the club’s other key players departed, and the threadbare squad soon proved to be inadequate. Coach Kulak proved to be an early casualty, with reserves coach Goran Runje taking his place. But, despite these changes, the club was not able to able to avoid relegation and found itself back in the Second Division for the 1999 season. The appointment of experienced campaigner Paul Rolleman as coach helped to stem the flow of players leaving the club and, with a core of talent to build around, the club struggled through the 1999 season to eventually finish twelfth out of the fourteen teams.