Relative success in the following years paled into insignificance following the FA Amateur Cup run of 1967/68 when, against all the odds, little Chesham United went all the way from the Preliminary round to the final of the FA Amateur Cup, finally losing 1-0 to Leytonstone in front of a 54,000 Wembley crowd. At a time when the population of the town was just 18,000 people, the club sold 22,000 tickets for this game.

The club went into turmoil on May 3rd 1983 when the main stand burned down. A new stand was officially opened with the visit of a Watford side, managed by the late Graham Taylor in 1984. The 1987/88 season marked the centenary of non-league football in the town of Chesham, an achievement commemorated with a match against a full-strength Arsenal side on 18th August 1987. In 1991 the club won the Isthmian League Division One title and also reached the final of the inaugural Loctite Cup but lost to Bishops Stortford on penalties. In October 1992 the club went to the very top of the Isthmian League after a famous win at Enfield and stayed ahead of the pack until the end of the season, being crowned Champions on the last day after a 4-0 win over Dulwich Hamlet.

That season the average gate was just short of 1,000. The season also saw the arrival of ex-Liverpool star Mark Lawrenson. However the season ended in disappointment when promotion to the Conference National was denied because the club could not afford the necessary ground improvements. Since those days the club has been through many managers, including ex-England internationals Graham Roberts and Luther Blissett and literally hundreds of players, including a stint with Bruce Grobbelaar between the sticks.

In the early 2000s the club again had an eye on promotion to the Conference as Bob Dowie led a strong Chesham side to 6th in the Ryman Premier, possibly an under-achievement when considering the resources at his disposal. The team that year included Wayne Andrews and Fitz Hall, both of whom went on to enjoy professional careers in the higher echelons of football. Two years later and the club were once again relegated back to Division One.

With re-structuring on the horizon, the 2003/04 season was all about finishing in the top six. After an indifferent start the team climbed up the table to eventually take 4th spot in the Ryman Division One (North) and earn a place in the Southern League Premier Division. United’s first year in the Southern League was certainly adventurous. At times they looked title contenders, then flirted with relegation and in the end were happy to finish in mid-table.

The following year the true price of years of over-achieving came to light. Nearly two decades of wealthy chairmen helping to fund the club was over and it was time for the Generals to stand on their own feet, a task that proved too much. By February 2006 the club was truly on its knees. The front pages of local papers were highlighting the sorry plight of the club that had seen so much. A public meeting was called at the Town Hall to “Save Chesham United” – it was a last desperate throw of the dice. Fortunately the sorry tale had a happy ending. A local businessman, Charles Manchester, read the stories, visited the Meadow, showed an interest and helped get the club back on its feet.

His intention was always to hand over the club to its supporters and he gradually brought more members of the Chesham United Supporters’ Trust onto the main club board whilst other Trust members took on many of the day to day tasks of running the club. Fittingly, after for years at the helm, he was able to stand down at the end of the 2009/10 season with promotion back to the Southern League Premier Division secured and the club back on a stable footing. After good work by the Supporters’ Trust, the club’s financial position was improved following a takeover of the club by businessman Roger Payne in 2012. This takeover allowed Chesham to consistently challenge for promotion to Conference South in the following seasons.

Following relegation to the Southern League South & West Division in 2006, Chesham were transferred to the Midland Division after a single season. In 2007/08 United finished 6th and missed out on the play-offs on goal difference, but in 2009 finished 5th, but lost in the play-off semi-finals to two late goals at Nuneaton Town having led 1-0 for much of the game.

In 2009/10 a fourth-place finish was enough to reach the play-offs again. A 1-0 victory away at Burnham set up a final against Slough Town with a crowd of 1,115 witnessing a 4-0 victory at the Meadow to secure promotion. Consolidation in the Southern League Premier was the main aim for 2010/11, but Chesham United finished 6th in the league having been in the play-off race for much of the campaign. They achieved a 4th place finish in the 2011/12 season, losing in the play-off semi-finals to AFC Totton. In the 2012/13 season Chesham reached the FA Trophy Second Round, whilst in the league were unbeaten in their last 17 games to finish 3rd, before losing to Hemel Hempstead Town in the play-offs.

Chesham were able to build on this in the 2013/14 season, pushing eventual champions Hemel Hempstead Town all the way in the title race, but eventually had to settle for a place in the play-offs. After beating Stourbridge 2-1 at the Meadow in the play-off semi-final, Chesham lost 3-1 to St Albans City in front of a crowd of 2,960, the largest seen at the Meadow for many years. However a number of players left the club in the following close season and a revamped squad finished in 11th position.

The 2015/16 season saw history made as Chesham knocked a Football League team out of the FA Cup for the first time, beating Bristol Rovers 1-0 on their own ground in the First Round proper. This led to a trip to Bradford City’s Valley Parade ground in the Second Round, when two late goals gave the home team a flattering 4-0 win. In 2016/17 Chesham again reached the FA Cup First Round proper, losing 2-1 to Peterborough United at London Road. This resulted in a fixture backlog which led to the club finishing 11th in the league for the third season running.

James Duncan and Michael Murray took over as joint managers in October 2018 with the team bottom of the table with just one point from eight games. They turned the team’s fortunes around to such an extent that the club finished in a comfortable tenth position. The club continued to progress and were second in the table when the league season was cancelled in March 2020 due to the coronavirus pandemic. In 2021/22 the club finished sixth and just missed out on a play-off place, but the following season went one better only to lose in extra time to Bracknell Town in the play-off semi-final. However the club put this disappointment firmly behind them with a magnificent season in 2023/24, winning the league by nine points to reach the National League for the first time, before going on to finish 13th