Len Pickard was signed on amateur forms from Barnstaple, on the 4th  October 1947, making his debut against Torquay in the Southern League Cup on the 8/10/1947. He scored the final goal in 2-2 draw.

In May 1950, he was played and scored for Barnstaple in front of a crowd 7000 fans against Bideford in the Westward Hoe Cup at the United Services ground in Barnstaple.