Morris defeated Robertson for the first time in a friendly match in 1843, winning a jacket, but the two generally did not compete head-to-head for stakes.

Robertson, as the acknowledged best player, could refuse any challenge according to the custom of the time, and said he preferred Morris as his playing partner; Morris was in an awkward position with respect to individual playing reputations, since he worked for Robertson, who eventually fired him after a disagreement over equipment.

Challenge matches, usually backed by noblemen and wealthy businessmen, were the main form of golf competition at the time.

The out-and-back flow of play over a narrow strand of fairway at the Old Course eventually led to the establishment of huge double greens, virtually unique in Scotland; these have occasionally been imitated in modern golf design.

Robertson's first golf course design work, in which he was assisted by Morris, was at Carnoustie in 1842, when the two laid out ten new holes.

Morris accepted the march of progress and felt obliged to leave Robertson and set up his own workshop.

Morris moved to Prestwick in 1851, on the west coast of Scotland, to build a new golf course, where he served as professional and greenkeeper.