The year 1989 proved difficult, and the Gamblers could only manage a second-to-last place in the newly organized Verbandsliga Hessen. However, 1990 saw a comeback with them winning the Verbandsliga Hessen championship, this time undefeated and with an impressive record of 52:16 points. These successes, however, could not lead to promotion to a higher league, as a restructuring of the federal leagues prevented this.
It was only a year later that the Gamblers were promoted to the Second Bundesliga Mitte and proved their strength with a second-place finish in their first season there. The American Football boom fueled by the Frankfurt Galaxy contributed to the further popularization of the sport between 1991 and 1992. In 1993, league reductions complicated game planning, but the Gamblers still became champions of the Second Bundesliga Mitte. Despite successful relegation playoffs, the use of an unlicensed player prevented promotion to the first league.
In 1994, the Gamblers, led by Head Coach Tracy A. Holland, participated in the Football League of Europe (FLE), which led them into financial difficulties and ultimately to the club's insolvency. In the same year, the high travel costs and sporting failures prevented sustained operations, which halted continued play in the Second League.
Parallel to the men's team, the youth division of the Frankfurt Gamblers was founded in 1990 under Klaus Possinke. Under head coach Steve Smith, the youth team won the Hessen championship in 1992 and repeated this success in 1994, although the season was overshadowed by the unexpected death of an important player. The season ended with a defeat in the Junior Bowl against the youth team of the Berlin Adler. This participation in the final for the German youth championship was the club's greatest success.
From the ashes of the insolvent club, the "Frankfurt Knights" club was then formed in 1995, which, however, only had short-term success and also went bankrupt. The nine years of the Frankfurt Gamblers' existence were marked by sporting highlights and economic lows and left a formative influence on the history of American Football in Frankfurt.