Pleass was a follower and played his early football at South Melbourne when they were in the Victorian Football Association (VFA).
He participated in their inaugural VFL match and remained with the club until 1904 when he crossed to Essendon, after his transfer to play for Boulder in the Western Australian Goldfields was refused. During his career he represented Victoria at interstate football on three occasions.[2]
A ruckman, Pleass briefly gave the game away in 1902 to become a field umpire but returned to South Melbourne after officiating in a couple of games.[3]
1899 team of "champions"
At the end of the 1899 season, in the process of naming his own "champion player", the football correspondent for The Argus, Reginald Wilmot ("Old Boy"), selected a team of the best players of the 1899 VFL competition:
From those he considered to be the three best players — that is, Condon, Hickey, and Pleass — Wilmot selected Pat Hickey as his "champion player" of the season.[4]