He joined Richmond from Echuca in late 1920, and played in two games – the club's round 18 match and its semi-final – to high acclaim, before his permit was revoked after it was determined that he was tied to Essendon's district and was ineligible to play for Richmond;[2] Ogilvie had lived in Essendon's district prior to the World War I, and although he served almost three years in France during World War I, the time away was not long enough for Essendon's residential claim to him to have expired.
[4] He was a member of Port Melbourne's 1922 VFA premiership team; Ogilvie alleged that one of his Footscray opponents offered him a bribe during the Grand Final to throw the game – similar accusations were made against other Footscray officials – but there were no corroborating witnesses and the allegations were not upheld.
[5] Ogilvie returned to live in Echuca in 1923, but continued commuting to play with Port Melbourne until the end of the 1924 season.
In 1934, South Melbourne captain-coach Jack Bisset went as far as naming Ogilvie as the best player he had ever seen, even ranking him above legend Haydn Bunton, Sr. (who at that time was four years into his career).
[10] He is considered one of the best players ever to play in the Bendigo Football League, and a rivalry trophy named in his honour is contested between his two country clubs, Echuca and Rochester.