Playing with Richard Emery, Jackson won the 1968 Piccadilly Fourball Match Play. From 1964 to 1967, a 72-hole stroke playPiccadilly Tournament competition had been played on the East Course at Wentworth prior to the Piccadilly World Match Play Championship but in 1968 this was replaced by a four-ball better-ball match play tournament. 32 pairs competed in the knock-out competition, each round over 18 holes of the East Course. The plan was to play the first round on Monday 7 October, followed by two rounds on each of the following two days. However, heavy rain on the second day meant that the third round could not be played that day and the final was delayed until Thursday 10 October, the same day as the opening round of the 1968 Piccadilly World Match Play Championship.[3] Jackson and Emery beat Neil Coles and Bryon Hutchinson 2&1 in the final and won £500 each out of the total prize money was £4,000.[4]