The Management Committee decided that a professional coach was needed to revive the club's fortunes, hence the introduction of Les Henley. Sydney Black, the Club Chairman, recalled that he had consulted Ted Drake, a former colleague of Henley at Arsenal and manager of the Chelsea team which had won the League Championship in 1954-5 and it was on Drake's recommendation that Henley arrived.
Black had also asked the Football Association for a list of recommended coaches and Henley's name was at the top of the list. And top billing he had, being given full responsibility for the coaching and selection of the first team, so becoming the first manager, in the modem sense of the word, of Wimbledon Football Club.
The first team began training under floodlights for the first time before the season proper began with an encouraging 4-2 victory over Ilford, but this was followed by only one draw in the next three games, as Wimbledon settled into a mid-table position. In the FA Cup, Wimbledon defeated Edgeware in the preliminary round 4-1 after a goal-less first half. The attendance of 2,980 was very disappointing, compared to the 10,600 against Kingstonian six years earlier in a first qualifying round match at Plough Lane.
A second-half penalty duly saw Finchley end Wimbledon's hopes at the next hurdle. Wimbledon had adopted a different style of play, one based on the 'M' formation developed in England by Don Revie at Manchester City. This involved the centre forward playing in a more deep-lying role, hopefully pulling a centre half with him, while the two inside forwards pushed up more.
But spectators were becoming frustrated by the lack of success on the field and matters came to a head during the home game against Bromley. While a Wimbledon player lay injured, one of the spectators jumped over the railings, and remonstrated with the referee. He was escorted off the pitch by the players, but stones were also thrown, and the club warned the fans that any repetition of such behaviour could result in FA disciplinary action.
The lack of success also affected some of the players. As amateurs, they were not bound to the club and so could be poached very easily by the more successful sides. Wimbledon had already lost a couple of players and in November, star man Jeff Darey opted out. Darey, who was in the squad for the Great Britain Olympics football side, decided to switch to Athenian League Hendon and his move led to some angry letters to the local Press complaining about the lack of ambition at the Club.
Wimbledon's performances were very inconsistent, with good home form countered by poor displays away. One week League leaders Romford were beaten 1-0 at Plough Lane, while the next the Dons slumped 5-1 at Woking.
Athenian League Wealdstone were the visitors in the London Senior Cup and although they went ahead early on, Wimbledon recovered to win 4-1, including the first hat-trick of the season by Joe Wallis, one of three Wallis brothers to play regularly for the Dons in 1955-6. Jack Wallis scored the other. But goals from these two Wallis brothers were not enough in the Second Round, when Corinthian Casuals won 3-2 at Plough Lane.
Wimbledon began their defence of the Surrey Senior Cup at Walton & Hersham, where they fought out a 2-2 draw before winning the replay fairly easily 2-0. The second round took the Dons to Fetcham Grove to meet Delphian Leaguers Leatherhead, where a record crowd of 1,300 was present. On a very poor pitch, Wimbledon missed countless chances before Joe Wallis put them ahead in the 55th minute. He was carried off unconscious after Leatherhead had equalised, however, and the home side scored twice more in the closing five minutes to win 3-1.
The Amateur Cup trail began at Enfield, where a disastrous start saw Wimbledon go behind in the fourth minute. But Joe Wallis equa1ised in the fifth minute with a header and Wimbledon went on to dominate the first-half. In the second period it was a different story as Enfield pressed hard for a winner, but Phipps missed a glorious chance for the home team with minutes to go and Wimbledon held out for a draw.
In the replay at Plough Lane, a crowd of over 3,000 saw Wimbledon score three times in the first-half on a mud bath of a pitch and Enfield could only manage one second-half consolation. That was it though, for in the second round tie at the Oval, Wimbledon outplayed Corinthian Casuals but lost 3-2.
The programme price had stayed at twopence since 1946, but mounting costs forced Wimbledon to increase the price by a penny before the home game against Clapton, which was lost 3-0. A run of poor results led to still more frustration and after the game against Leytonstone trouble erupted again. The referee was punched and kicked on the way to the dressing room and left the ground with a jaw injury.
For their part in the affair, two Wimbledon players were disciplined by the FA, one being fined one guinea, while the club was also ordered to display a warning in the first four programmes of the next season, stating that a repetition might lead to the ground being closed. With five games to go, Wimbledon were 13th, out of 15, with 18 points from 23 games, but won their four remaining home games to finish 11th.
The season finished with Tony Wright, a recent signing from Carshalton Athletic, scoring seven times in the last three games, including a hat-trick in the final 5-1 victory over Dulwich Hamlet. Joe Wallis remained top scorer with over 20 goals in the season.
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