Esling was engineer-in-charge in the Way and Works branch of the Victorian Railways department, located at Flinders Street.

While Gossip was considered to be strong than any other Australian/Victorian chess player at the time, Esling, also a leading Melbourne player, accepted the challenge and won the first game with the 2nd game being adjourned in favourable position, after which illness forced Gossip to forfeit the match.

[6] Esling finished second in the Second Australian Championship, a tournament held at Adelaide 1887, with 7 out of 9 points, behind Henry Charlick (7.5) but ahead of Gossip (6.5).

[5][7] In 1895, Esling challenged Alfred Edward Noble Wallace of Sydney, the reigning Australian champion, to a match for the title.

In a letter published in The Sydney Mail, he graciously wrote that "after the close fight we have had, I cannot as much as I would like to - think myself a better player than my late opponent, F.K.