He had considerable early success as a young professional from 1960 to 1963 but then had a lean period, partly due to a stomach ulcer.

[1] He was briefly an assistant at Sunningdale, during which time he won the 1960 British Youths Open Championship at Pannal Golf Club by 7 strokes.

[5][6] In the 1964 Swallow-Penfold Tournament Caygill led Peter Alliss by 3 strokes with 5 holes to play but finished badly to drop into a tie for second place.

[14] In 1970 Caygill had his only foreign win, the Lusaka Dunlop Open on the Safari Circuit, finishing two strokes of Craig Defoy.

[20][21] In 1981 Caygill was fined £500 and suspended by the PGA following an incident the previous October at the Wansbeck Classic, a pro-am event.