The 90's turned out to be the decade of 'the good, the bad and the ugly'.  The good came in the form of the plethora of trophies won, the bad was the passing away of a number of former and serving club officials and the ugly was the arrival of a new batch of players like Simon Hardle, Jamie Perkins, Matt Gould, James Wood and Pete Oakley.

The decade began with a close season football tour to Haselunne Sportsverein of Germany in May 1990.  Some of the stories to make it through censorship included allegations of a strange man greeting our current Chairman's wife Helen Phillips as she left the shower, late night drinking in Bimbo's Cellar Bar and the occasional football report.

In November 1990 Cec Patten severed his formal links with the club after more than sixty years of service when he retired to Wales.  Cec had served the club in many roles including Match Manager, AFA Representative, Chairman and President as well as refereeing a game when he was over seventy years old.  In 1992 was bestowed with the title of Life President of Old Wulfrunians' Football Club and continued to keep his connections with the club by acting as a 'Welsh Correspondent' for the Condor Times newsletter.

For the 1989/90 season John Turvey was installed as captain of the third XI.  By the end of the 1990/91 season he had guided them to a glorious relegation, but bar profits had received a tremendous boost.

For the 1991/92 season Dave Pointon and Alan Thompson had built possibly the best ever team to represent the club (with the exception of the current first XI - DOP), a team so packed with stars it was nicknamed 'The Harlem Globetrotters'.  They took on all-comers during this season and usually came out on top.  They won the Premier Division title, the J.W. Hunt Cup and also supplied many players for the Veterans to win the London AFA Open Veterans Cup for the first time.  Unfortunately their success had also attracted an unruly crowd, young spectators came to watch first XI games, not for the football, but to listen to "some serious swearing from Mick Brayshaw".  The second XI also finished runners up in the Junior Cup.

Success for the club continued in the 1992/93 season, the fourth XI won the Holder Cup, the Veterans retained the London AFA Open Veterans Cup and the first XI finished runners up in the J.W. Hunt Cup.  There were two low points during this season.  The first was the sad loss of Tony Howard, father of Mark 'Snowy' Howard.  The second was Mick Brayshaw being sent from the ground at GEC Avery for inciting a riot.  A chastened Brayshaw slunk from the pitch but was seen peering around the pavilion to watch the rest of the game.

By 1993/94 the success was starting to diminish, the first XI could have won the league title with victory on the final day of the season but a poor refereeing decision consigned them to finishing third.  A couple of success stories that did arise this season were the first edition of the Condor Times newsletter and the first use of Molinuex Stadium for the Annual Dinner.  This season also marked the retirement of Groundsman Les French after years of excellent service, to be replaced by the equally able Tom Mitchell.