Season 1933-34 saw an epic Scottish Qualifying Cup Qualifying Round tie with Gala Fairydean, which stretched to three dramatic matches watched by some four and a half thousand people. A special train ran supporters to Galashiels for the match, which ended in a 3-3 draw after Vale had been 3-1 down. The replay saw another specially laid on train come from Galashiels and with 10 minutes of the match remaining Gala were 2-0 in the lead, but in a grandstand finish, Vale netted a last minute equaliser. This was before penalty shoot-outs decided games, so the game went to a second replay with Vale winning the toss for the right to host it. This time after 30 minutes Vale held a 4-1 lead, but Gala striker Sherlaw completed a hat trick in the second half for a nailbiting finish to the match, but Vale held out for a 4-3 win.

In the Scottish Cup Vale were drawn against the Qualifying Cup winners Rosyth Dockyard Recreation at home and won 3-0. In the next round they were drawn against Scottish Division One team St Johnstone, again at home. Half time saw the game poised at 1-1, but by late in the second half the superior fitness of the League side saw them scoring twice to win 3-1.

In 1934 Honourary Secretary Mr. Alex Crabbe intimated at the Annual General Meeting that he wished to give up the position, but was prepared to carry on for another year provided an assistant was found and proposed Mr. Edward B. Sanderson should be made Assistant Secretary. This was accepted and at the 1935 AGM Mr. Crabbe, who had held the position of Honourary Secretary for 42 years, retired and was replaced by Mr. Sanderson.

Season 1937-38 saw what proved to be the only trophy to be won by Vale during the 1930's - the King Cup, after a fine 4-1 victory over Chirnside United in a final played at Galashiels.

In 1938 Vale traveled to Edinburgh for a Scottish Cup tie with St Bernards. After a fine performance, Vale unluckily lost 0-1 and St Bernards then went on a run to the semi-final losing to the eventual winners East Fife. However St Bernards had been so impressed with the play of Vale left-back J Miller they signed him a few weeks after the tie. Other Vale players left to play League football; J Dodds & W Rathie joined Peebles Rovers before both signing for Hearts and Donald Murray who had originally come from Peebles Rovers, rejoined them before moving on to Ayr United and then St Bernards.

Also in 1938 it became known that Miss Hay of The Ley had a shooting lodge that she wished to have removed. Vale expressed an interest through the joiner Bob Scott and the result was that Vale could have the building provided they removed it. The structure was transported to Victoria Park, where it was re-erected at the east end of the ground. Miss Hay was so pleased with the tidy state of the site where the lodge had stood, she sent a cheque for two guineas, which was quite a nice donation in those days!

World War broke out again on the 3rd of September 1939. Once again organised football was curtailed and Vale players were called up.