The promised floodlights went up during the close season and although Wimbledon were drawn away at Arsenal in the London Challenge Cup, The Gunners were persuaded to come to Plough Lane for floodlighting up time later in the season. The opening game of the campaign was the 1959-60 South of the Thames Cup semifinal and after a 1-1 draw against Bromley, the match was decided on the toss of a coin. Visiting Secretary Charlie King called correctly, and Wimbledon were out.
The League season started promisingly, Wimbledon winning 2-1 at Oxford City with two late goals and then 8-1 at Ilford. Woking were the visitors in the FA Cup first qualifying round and their resistance crumbled in the second-half, as Wimbledon won 5-1, including four headed goals.
In the next round, Wimbledon met Dorking for the third successive year and started disastrously, going 2-0 down after eight minutes. Wimbledon gradually took control and shortly after half-time scored twice to lead 32 only to fold ignominiously as Dorking scored twice in the last 15 minutes to win 43.
The much awaited Arsenal match took place on October 3 and 8,900 spectators saw Arsenal outplay the Dons to win 4-1. Soon afterwards, Ted Murphy joined from Tooting and Old Dons' stalwart Jimmy Wright made the reverse journey. International honours came for Wimbledon, with Roy Law being picked for England Amateurs against Wales and John Martin also being selected.
2,400 spectators would be present for the Dons 3-1 victory over St. Albans City in the league (match report) Away from home, Wimbledon had been finding the going hard, but in December they hit a purple patch, winning 4-1 at Corinthian Casuals and 2-1 at Dulwich, a game in which Mike Kelly made his first team debut. And in the London Senior Cup first Round, Athenian League Leyton were trounced 9-0, with Reynolds scoring a hat trick.
In the Surrey Senior, Wimbledon comfortably saw off Dorking 3-0, before defeating Tooting and Mitcham 2-1 in a Boxing Day derby to remain well placed in the League.
The latter part of this match was played under floodlights, but Tooting refused to play under lights for the Surrey Senior Cup tie 12 days later. Their lights duly went out, as a Kenchington hat-trick saw Wimbledon home 5-0. (match report)
Wimbledon came from behind at halftime to win 2-1 at Barking in the London Senior Cup and then played brilliantly at Bromley, winning 3-2 at one of the title favourites. In the first round of the Amateur Cup Wimbledon received the most difficult draw, away at Wycombe Wanderers, where they hadn't won in 25 years.
Before a crowd of over 5,000, Wimbledon dominated the early exchanges, only to fall behind before Reynolds equalised just before half-time. The second-half was fairly even, but as the game went on Wycombe gradually got on top until, on a breakaway in the 87th minute, Norman Williams scored a brilliant goal to seal a Wimbledon victory.
Wimbledon were drawn at Woking in the next round and there was a pre-match dispute when Wimbledon were offered only 30 stand seats and in the end declined to take any. Wimbledon fell a goal down after 40 seconds, but two from Kenchington helped them to a comfortable 5-1 win.
Another goal was conceded in the first minute in the next game against Carshalton Athletic in the London Senior Cup, but this time Dons never really recovered and lost 32.
Wimbledon's third round Amateur Cup opponents were Whitley Bay, who were lying second in the Northern League. In a good game, Wimbledon went ahead early on, and Reynolds added another shortly after the interval. But Whitley Bay were a good side and scored twice midway through the second half to draw level. It looked as if Wimbledon had clinched victory, however, when Hamm scored a brilliant goal in the 86th minute, but a lack of concentration in defence allowed Whitley Bay to equalised a minute later to force a replay at Hillheads Park. The attendance of 7,780 was the largest Amateur Cup gate of the day.
Because of an England international game, Wimbledon managed to get the replay put back a week and four days before traveling north the Dons opened the Kingstonian floodlights by winning 3-1 in a League match.
Wimbledon made the perfect start at Whitley Bay, with Reynolds scoring early on and Wimbledon dominating the next half hour. But Whitley Bay scored a shock equaliser in the 35th minute and Wimbledon were forced to hang on. They had a brief spell on top and Hamm scored to put the Dons back in front, but Whitley Bay pressed continuously and a quite brilliant 40-yard shot gave them the equaliser in the 80th minute. Kelly had to play really well as Whitley Bay poured forward in extra rime, but Wimbledon held on and won the toss to choose a venue for the second replay, opting to play at Kingstonian.
Interest in the tie was so great that 9,870 turned up at Richmond Road and the gates had to be closed with many hundreds locked out. The floodlights failed shortly before kickoff but power was quickly restored and at half-rime, Whitley Bay must have wished that the lights had stayed off. Wimbledon had produced their best football of the season to score four goals without reply. Whitley Bay scored immediately after half-rime, but Brian Martin scored twice more to complete a hat trick as Wimbledon won 6-1 to move into the Quarter Final.
Four days after the third match of their Whitley Bay epic, Wimbledon entertained Walthamstow Avenue in the Amateur Cup quarter-final and 10,806 fans, the largest crowd at Plough Lane since the teams had met in the same round in 1952, turned up.
Wimbledon, though, looked jaded and although dominating territorially, they lacked a finishing thrust.
It was Walthamstow who took the lead when Minall scored from a quite brilliant move in the 46th minute. After this, Wimbledon pushed forward re1entlessly, but they persisted with long high balls down the middle and Walthamstow clung on to win 1-0. Like Hendon the season before, they went on to win the Cup. Their title hopes finally ended at Maidstone where they lost 1-0, but on the following Monday they took the South of the Thames Cup by beating Bromley 5-2.
The title was now between Bromley and Walthamstow Avenue and Walthamstow came to Plough Lane needing one point to secure an Amateur Cup and Isthmian League double. Ardrey missed a penalty but rain caused the match to be abandoned after 30 minutes with no score.
It was replayed the following night and Wimbledon avenged their Amateur Cup defeat 3-2, letting Bromley in to take the tide by one point. Wimbledon finished third. But at the annual meeting that close season, Wimbledon supporters were accused of lacking sportsmanship, too quick to knock the players when things went wrong.
It was pointed out that Wimbledon's away form was worthy of the Champion's 20 points from 15 games, but that the home form was disappointing, producing just two points more. Some of the players said that they preferred playing away from home.
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