 Trott made his first-class debut for Victoria against an "Australian XI" on New Year's Day 1886, scoring four and 18 not out. Two months later, he played his first inter-colonial match, against South Australia at the Adelaide Oval. Batting, he scored 54 runs; his innings included a memorable hit over the leg side boundary from the bowling of leading Test all-rounder George Giffen, and he captured seven wickets for the match with his bowling. In 1886 – 87, Trott hit a double century for South Melbourne in a match against St Kilda and appeared for Victoria against Alfred Shaw's touring English team, claiming four wickets for 125 runs (4 / 125). During the next summer, he played for a non-representative "Australian XI" against Arthur Shrewsbury's XI and George Vernon's XI, two English teams touring Australia simultaneously. His chances for inclusion in the Australian squad for the forthcoming tour of England were enhanced when a number of leading players made themselves unavailable. However, Trott's batting credentials were modest: he had scored only one half-century in 29 first-class innings. At this point, Trott had enjoyed more success with his bowling. Prior to the Australian team departing for England, a change to the leg before wicket (LBW) law that would aid bowlers of Trott's style seemed imminent. The former Australian player Tom Horan wrote: "There is no bowler in England who has such a fast leg-break, and on a fine, firm pitch many a batsman has saved his wicket by his legs or body in opposing Trott's deliveries."
