The financial situation was still poor and even Henley had a price to pay when he was offered the same wages, but his accommodation allowance was withdrawn. Poole Town offered £500 for O'Mara, and were turned down flat and O'Mara promptly scored a hat-trick as Wimbledon crushed Crawley Town 9-0 in the League.
A new competition for senior non-league teams, the FA Trophy, had started and promised a Wembley Final. Wimbledon were drawn away in the first round at Dartford and there, their hopes died in a 3-2 defeat.
On the League front, Wimbledon briefly moved to the top after beating King's Lynn 2-1 at home, but the lead didn't last long. They had, however, moved easily into the Southern League Cup quarter-final, where they were drawn at home to Cambridge United. But after Hodges had scored a glorious goal in the 30th minute, the visitors began to get on top. Guy stood tall in a rearguard action, however and Wimbledon held on to move into a semi-final showdown with Bedford.
The visitors looked capable of keeping Dons at bay, but in the 79th minute, to the great relief of the home fans, O'Mara tapped in a Hodges cross and Wimbledon held on to earn a final place against Romford.
Wimbledon had moved back to the top in the League as well, but others had games in hand and a 1-0 defeat at Hillingdon on March 21 saw them knocked off pole position. Any title hopes died yet again, over the Easter period, when the Dons lost 2-0 at Romford and 5-1 at Margate, although an injury-hit Wimbledon side had held Margate to 1-1 until the final 20 minutes.
The Southern League Cup was now their only chance of glory. The first leg of the Final was at home to Romford and Wimbledon made a dream start. Romford's offside trap was breached in the third minute and Obeney could only deflect a shot past his own 'keeper. Three minutes later, O'Mara scored with a brilliant header and Davies made it 3-0 at half-time. Romford pressed continuously from then, but Wimbledon held out to take a three-goal advantage to Brooklands. The only disappointment was the crowd of only 1,505.
It looked as though Wimbledon would need all that advantage in the second leg as they were forced to defend desperately. Romford scored in the 12th minute to keep their hopes alive, but five minutes before half-time O'Mara equalised and in the second half Wimbledon began to improve, holding out for a comfortable 1-1 draw and an aggregate 4-1 win to lift the Worcester Vase for the first time.
Wimbledon finished fifth in the Southern League, eight points behind Champions Cambridge United, who were promptly admitted to the Football League in place of Bradford Park Avenue.
Wimbledon made a small profit, but would have lost money without Sydney Black's £7,000. Gates had declined further to an average 1,820 for Southern League matches and only 490 for Premier Midweek Floodlight League matches.
Admission prices for Southern League matches were raised to five shillings and with Len Hibberd unable to continue as Chairman, Stan Jasper was elected. He was in favour of a reserve team and it was thought that some friendlies might be played in 1970-1 against Amateur Football Alliance teams.
Alan Burton, who had scored the Championship-winning goals at Dulwich in 1959 before turning professional with Aldershot, now re-signed for Wimbledon on a free transfer. And Wimbledon had hopes of signing another former player in Johnny Haynes, who had played a few games in the 50s. But the former Fulham and England player decided to accept an offer abroad instead.
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