Opperman was born in Rochester, Victoria in 1904 of British-German descent.
His father, Adolphus Samuel Ferdinand Oppermann, had worked as a butcher, miner, timber-cutter and coach driver.
Hubert, the eldest of five children, learned as a child to plough with six horses and to ride bareback.
He attended several schools and delivered Post Office telegrams by bicycle.

Some time following Hubert's birth, his parents moved to Western Australia, along with his uncle Albert Oppermann and his father's cousins August, Emil and Hugo Oppermann. (
Hubert's grandfather, Otto Friedrich Oppermann, was one of three brothers who migrated to South Australia as miners in the 1850s; two brothers remained in South Australia, while Otto came to Victoria).

Hubert's sister Winifred was born in Western Australia in 1907; after that the family moved back to Victoria where Hubert's twin siblings Bertha Ellen and Otto Alexander were born in 1910, followed by younger brother Bruce some years later.
 Bruce also became a competitive cyclist, and won several regional races in Victoria.

It is not known when, or why, Hubert anglicised his surname and dropped one 'n' from its end.

He came third in a cycling race at 17 in 1921.
The prize was a racing bike by Malvern Star Cycles, a cycle shop in the Melbourne suburb of Malvern.
The proprietor, Bruce Small, was so impressed he offered Opperman a role in the business, which helped turn both into household names in Australia.

Opperman is the only rider to have won the Australian national road race title four times, in 1924, 1926, 1927 and 1929.
The 1924, 1926 and 1929 titles were awarded for winning the Blue Riband for fastest time in the Warrnambool to Melbourne Classic.
 In 1927 the Warrnambool to Melbourne was not run and the title was won by Opperman as the winner of the Dunlop Grand Prix, a 690.5 miles (1,111.3 km) race over four stages.

In the Goulburn to Sydney Classic Opperman was first and fastest in 1924 and 1929 and was fastest in 1930 setting a new race record.

Opperman was critical of the handicap races then prevalent in Australian cycling Opperman's plea for scratch racing was partially met in 1934 in the Centenary 1000, a one-week road bicycle race over seven stages covering 1,102 miles (1,773 km).
The championship was based solely on time, although there was also a handicap race with riders divided into 4 grades.
The race was run in as part of the celebrations of the Centenary of Victoria.
Opperman had injured his knee in a fall in stage 4 near Wangaratta, but despite this he was still well placed at 3rd in the championship.
He injured his knee again in a fall whilst descending from Mount Hotham.
 Opperman also cut his hand requiring stitches, which he refused until after the stage.
He battled on to Sale, losing 27 minutes on the stage to Lamb.
  He attempted to finish the race, but was forced to abandon at Traralgon, said to be the first time Oppy had retired from a race.
Opperman was born in Rochester, Victoria in 1904 of British-German descent. His father, Adolphus Samuel Ferdinand Oppermann, had worked as a butcher, miner, timber-cutter and coach driver. Hubert, the eldest of five children, learned as a child to plough with six horses and to ride bareback. He attended several schools and delivered Post Office telegrams by bicycle.
Some time following Hubert's birth, his parents moved to Western Australia, along with his uncle Albert Oppermann and his father's cousins August, Emil and Hugo Oppermann. (Hubert's grandfather, Otto Friedrich Oppermann, was one of three brothers who migrated to South Australia as miners in the 1850s; two brothers remained in South Australia, while Otto came to Victoria).
Hubert's sister Winifred was born in Western Australia in 1907; after that the family moved back to Victoria where Hubert's twin siblings Bertha Ellen and Otto Alexander were born in 1910, followed by younger brother Bruce some years later.  Bruce also became a competitive cyclist, and won several regional races in Victoria.
It is not known when, or why, Hubert anglicised his surname and dropped one 'n' from its end.
He came third in a cycling race at 17 in 1921. The prize was a racing bike by Malvern Star Cycles, a cycle shop in the Melbourne suburb of Malvern. The proprietor, Bruce Small, was so impressed he offered Opperman a role in the business, which helped turn both into household names in Australia.
Opperman is the only rider to have won the Australian national road race title four times, in 1924, 1926, 1927 and 1929. The 1924, 1926 and 1929 titles were awarded for winning the Blue Riband for fastest time in the Warrnambool to Melbourne Classic.  In 1927 the Warrnambool to Melbourne was not run and the title was won by Opperman as the winner of the Dunlop Grand Prix, a 690.5 miles (1,111.3 km) race over four stages. 
In the Goulburn to Sydney Classic Opperman was first and fastest in 1924 and 1929 and was fastest in 1930 setting a new race record.
Opperman was critical of the handicap races then prevalent in Australian cycling Opperman's plea for scratch racing was partially met in 1934 in the Centenary 1000, a one-week road bicycle race over seven stages covering 1,102 miles (1,773 km). The championship was based solely on time, although there was also a handicap race with riders divided into 4 grades. The race was run in as part of the celebrations of the Centenary of Victoria. Opperman had injured his knee in a fall in stage 4 near Wangaratta, but despite this he was still well placed at 3rd in the championship. He injured his knee again in a fall whilst descending from Mount Hotham.  Opperman also cut his hand requiring stitches, which he refused until after the stage. He battled on to Sale, losing 27 minutes on the stage to Lamb.   He attempted to finish the race, but was forced to abandon at Traralgon, said to be the first time Oppy had retired from a race.
Hubert Opperman