Oswald originally played for
South Wanderers Junior Football Club in the
Wangaratta Junior Football League (WJFL), winning the Under 18 WJFL best and fairest in 1950, before making his senior football debut with
Wangaratta in the
Ovens & Murray Football League(O&MFL) in 1953. After a standout 1957 season, where he won the league goal-kicking award, shared the O&MFL
best and fairest, represented the O&MFL in the Victorian country football championships, and then kicked the winning goal for Wangaratta against North Albury in the 1957 O&MFL grand final. Oswald was then recruited by
Victorian Football League (VFL) side,
St Kilda. He played as a roaming
centreman for the Saints, and was considered the best in the state in that position from 1960 to 1961 when he also won two
best and fairests. Oswald decided to leave St. Kilda after the
1963 VFL season and was captain / coach of
Strathmerton for nine years, leading them to the 1964
Murray Football League premiership and playing 210 games and finally retiring as a player at aged 37 in 1974! He was later named on the wing in St Kilda's Team of the Century and was inducted into the St Kilda Hall of Fame in 2008. ==References==