A right-handed batsman, Gregory was the first Australian national cricket captain, leading the side for the first three recognised Test matches between England and Australia in March and April 1877 and January 1879.

[2] David William Gregory was a man of striking appearance, he "looked like an Old Testament prophet not long out of training college.

Of the former, it was noted that he was a "marvel of patience at first, and then followed a grand display of good, punishing power, combined with a splendid defence".

[9] Despite his low average, however, it is illustrative of the conditions of the pitches on which he played that he would reach double figures on several occasions when other members of his team failed.

He enjoyed more success on his home grounds, scoring a career best 43 in the second Test against England in March 1877,[6] having made only one earlier in the second.

[14] Following what would be his last Test, Gregory captained New South Wales against the touring England team at the SCG in February.

When the New South Wales team batted and Billy Murdoch was adjudged run out, no new batsman emerged.

England players were sent to the pavilion, at which point it became clear that Gregory was insisting the match be halted while a new umpire was found.

[15] In his obituary Wisden described Gregory's batting style thus: "Like many Australian batsmen in those early days, he had no grace of style to recommend him, but his defence was stubborn and he lacked neither pluck nor patience", and attributed his lack of successful scores to the pitches rather than his talent.

[6] After retirement, Gregory was made honorary secretary of the New South Wales Cricket Association, and also stood as an umpire for a first-class match on 27 January 1892.