[2] He played for the Launceston Cricket Club and made his first appearance in the biannual Tasmanian intrastate matches between North and South in 1871–72.

Although Tasmania did not play another interstate or first-class match until 1877–78, Bailey established a reputation as "a particularly forceful hitter, his favourite stroke being a powerful drive".

[7] He made 3 not out at number 11 in the match against the MCC at Lord's in which the Australians won before the end of the first day's play.

In the first match back in Australia, Bailey broke his arm while fielding, and took no further part in the tour, or the 1878–79 season.

[11] After returning to Tasmania in the early 1890s he played one last first-class match, at the age of 39, against Victoria in Launceston in 1892–93.