He played a thoughtful studied game, simple in essence, but he was also a fast runner and began to score splendid goals with hard shots often from around the edge of the six-yard box.
[6][7] Pickering scored two goals in the FA Cup 5th round tie against Leeds United at Bramall Lane on 15 February 1936, in a match watched by a record crowd of 68,287.
He possessed a strong shot and played in 39 matches in season 1935-36, scoring 17 goals as Sheffield United reached the 1936 FA Cup Final.
Pickering partnered striker Bobby Barclay in the final against Arsenal at Wembley Stadium, and both impressed with their stylish distribution and approach play.
He played in wartime matches for Sheffield United, and made eleven appearances in the team which won the League North title in season 1945-46.