At the beginning of the season, there were 25 professionals on the club's books. Everything was looking rosy.
Wimbledon opened the new League season with a visit to Champions Weymouth and although going down 1-0 on an appalling surface. They recovered to win 5-1 at home to Guildford City in the next match. Dons gave their worst display for years, however, in the London Challenge Cup, losing 1-0 at home to Leytonstone, but gradually started to improve and a 2-1 win at Cheltenham ended the home side's unbeaten home record.
In the FA Cup fourth qualifying round, Wimbledon were drawn away to Fareham Town, who were then playing at Bath Lane. There was an enormous interest in the match and a black market developed in the stand seat tickets, where the 400 four shilling tickets were reputedly changing hands for up to 30 shillings.
Five coach loads of supporters travelled and the two teams found the fans only inches from the pitch. Some spectators climbed up neighbouring trees to get a good view and the crowd was officially recorded as 2,479. But if the home supporters were expecting a shock result, similar to the one when they had knocked Hendon out of the Amateur Cup two years earlier, they were to be sadly disappointed.
The Hampshire League side tried hard enough, but Ian Cooke put Wimbledon ahead in the 27th minute and O'Rourke scored twice in the 67th and 78th minutes to complete a 3-0 win and gain some personal revenge. He had been in that Hendon team of 1963-4.
Wimbledon had easily beaten Sittingbourne 13-1 on aggregate in the Southern League Cup, including a 10-0 win at Plough Lane, but, having been given a bye to the third round, they lost 1-0 at Hastings United. Bobby Smith, the ex-England and Tottenham player, scored the only goal.
Their League form remained good and they took nine points from five games to move fifth in the table, only two points behind leaders Corby Town.
Back in the FA Cup, Gravesend and Northfleet visited Plough Lane in the first round proper. After Cooke scored an early goal for Wimbledon, trouble erupted when a Gravesend player was sent off and the whole team headed for the tunnel. The Gravesend manager managed to persuade his team to continue and Cooke scored again to give Wimbledon a 2-0 advantage at half-time. Cooke was to complete his hat-trick in the second half, as Wimbledon won 4-1, but Brown was sent off to mar a good display in front of the largest crowd of the season so far, 5,089.
Two days later, Wimbledon crashed 5-1 at Bedford in the EPFL and Kelly suffered a fractured jaw in the closing minutes. Les Henley moved quickly, buying Frank Smith from QPR for £1,500 and he made his debut at Corby, performing heroics before O'Rourke scored a late winner. The following week, Wimbledon's 3-0 win over Wellington took them top of the table.
The new League Leaders moved confidently on to the FA Cup, where the draw for the second round had given them a home tie against Folkestone. But it was just one of those days. Over 7,000 fans saw Wimbledon do everything but score and Wimbledon gifted Folkestone victory with a freak goal in the 70th minute. There seemed no danger when a cross came over, but Smith collided with a defender and the ball bounced in off his chest.
The new floodlights were switched on for the first time during the match against Tonbridge and Wimbledon turned on a show worthy of the occasion, winning 6-1 with Cooke scoring three.
Wimbledon left it very late against King's Lynn, scoring three goals in the last eight minutes and although they won 5-1 at in-form Romford, were rarely producing Championship winning form.
Smith had by now established himself in goal and Kelly was not content to play in the reserves. Although Wimbledon had turned down a £5,000 Millwall bid for Kelly earlier they granted his request to go on the transfer list.
Wimbledon felt they had had a wasted journey at Kettering in the EPFL when the match was abandoned after 65 minutes because of fog, with Wimbledon leading 2-0. But the EPFL committee decided that the result should stand and one person who was particularly pleased was veteran striker Joe Wallis, whose first goal of the season had come at Rockingham Road
A 1-0 win at Guildford City took them back to first position, but the following week, the Dons lost 2-0 at Poole, slipped off the top and were never to return. Wimbledon drifted down the table, reaching seventh position, and with the table being very closely-packed, they could have drifted into the bottom half.
Kelly was eventually sold to QPR and Wimbledon ended the season quietly, finishing fifth, with 50 points from 42 games, seven points adrift of Champions Weymouth.
Wimbledon's average attendance for 1965-6 was 2,650, with EPFL gates averaging 1,350. At the League AGM, Wimbledon applied again for a League place, but this time received no votes. Wimbledon resigned from the Eastern Professional Floodlight League because of the traveling expenses involved, and entered instead the Premier Midweek Floodlight League, comprising mainly amateur clubs.
Wimbledon announced that eight players would be released, mostly from the amateur days. And among those departing was the legendary Reynolds who had said at the start of the season that this would be his last. The Amateur Cup winning hero moved briefly to Ashford, before returning to Ireland to play for Derry City.
At the Southern League meeting, it was decided to fall into line with Football League rules and permit substitutes from the beginning of the next season. The travel secretary reported good away support, having taken three coaches to most games, while the club colours were changed for 1966-7 from blue shirts and white shorts to blue shirts and blue shorts.
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