He was the youngest South African to score a first-class century, at the age of 16. He also achieved the highest first-class score in domestic South African cricket at the time, scoring 337 not out. Despite a first-class career spanning almost 20 years, sources such as the Herald Sun quote Cullinan as being Shane Warne's bunny.

Cullinan was also involved in an unusual stoppage when 'calamari stopped play'. During a regional match in South Africa, Cullinan hit fellow international Roger Telemachus for six, whereupon it ended up in the kitchen and straight into a pan of fried calamari. According to Wisden, "Daryll Cullinan hit a six into a frying pan. It was about ten minutes before the ball was cool enough for the umpires to remove the grease. Even then, was unable to grip the ball and it had to be replaced".

His highest Test score was 275 which was a South African record at the time (as of 2012 the highest score by a South African in tests is 311 not out by Hashim Amla versus England).

Cullinan averaged 12.75 against Australia, falling to Shane Warne on four occasions. Cullinan also fell to Warne eight times in One-Day Internationals.^[4]

Cullinan's career Test average of 44.21 is only surpassed by nine South Africans with more than ten Tests.^{[citation needed]}

Cullinan was the coach of the Kolkata Tigers in the Indian Cricket League.

In November 2013, Cullinan was sequestrated for failing to pay back Azrapix Investments CC R19300.^[5]