Roly Caird was among the first group of goal umpires specifically promoted from the VFL Reserve Grade to fill vacancies on the senior list. Prior to 1955 it was common practice for former field and boundary umpires to be immediately transferred to the goals despite having no experience in the ‘trade’. Caird made his VFL senior debut in round one 1955 at Princes Park where Carlton thrashed a hapless North Melbourne. The end of the following season saw Roly appointed to his first finals match – the first semi final between Footscray and Geelong.
It was one of the lowest scoring finals in years with neither side capable of goaling in the final quarter. Nevertheless it was exciting as they come with the Doggies scoring three late behinds to break a 15 minute deadlock and steal victory.
Over the next three seasons Caird worked his way through the finals series getting closer to the last week in September and in 1959 he was appointed to the Grand Final. Melbourne toweled up the Dons in a final quarter blitz but it was a day of highlights with Ron Barassi and Bob Johnson in mercurial form.
The 1960 Preliminary was another of Caird’s cracking finals. Played in mud and slush, Fitzroy and Collingwood slugged it out and at three quarter time the Lions led by eight points. Collingwood surged home at Roly’s end to snatch a five point victory.
It was to be Caird’s last final for ten years despite regularly umpiring in the home and away series. He umpired the 1965 Victoria v. South Australia clash – his third interstate appointment – and umpired some of the great full forwards in VFL history such as Hudson, McKenna and Wade. Caird’s final VFL season was the first to feature matches at VFL Park Waverley and Roly umpired there on three occasions. His final match was the First Semi Final that year, notable for the fact that it was Bobby Skilton’s only final and despite being sentimental favorites his Swans were well beaten by St.Kilda.
A regular member of the VFLUA Executive Committee, Caird became a Life member of the VFLUA in 1966