Madaschi was born in
Perth, Western Australia. He left
Perth Italia to join Italian Serie A side
Atalanta's youth team at the age of 15 in 1998. Madaschi was part of the Atalanta youth side that won back to back Primavera Coppa Italia (Italian Youth Cups) in 1999–00 and 2000–01, along with losing the Italian Scudetto (Youth Championship final) to Inter in 2000–01. He was loaned out to Monza in July 2001, but in the January 2002 window was re-called back to Atalanta to the first team squad. Adrian constantly made first team squads at Atalanta, but could never break into the then Serie A team. He was again loaned out by Atalanta to
Pistoiese for the 2002–03 season. But again, did not see much first team action. In October 2003, after mutually agreeing to terminate his contract with Atalanta B.C a year in advance, Adrian signed for
Partick Thistle in the
Scottish Premier League. Unfortunately, even prior to Madaschi's arrival, Partick were doomed for relegation that season to the
Scottish First Division. Madaschi though, got regular First Team Football, playing 24 matches and scoring 2 goals in his debut Scottish season in the SPL and 27 appearances and 2 goals in the following season in the First Division. Madaschi left the club in May 2005, to join
Dundee for the
2005–06 First Division season. Adrian had to leave the club at the start of December 2005 to cure a recurring
osteitis pubis injury back in Australia. Madaschi returned to Italy to join
Grosseto in January 2006 and remained at the club until the end of that season. He then joined
Portosummaga in the 2006–07 season. In the 2007–08 season, Madaschi and Portosummaga achieved promotion to Lega Pro Divisione 1 where the club has maintained its status. The end of the 2009–10 season saw Portogruaro-Summaga finish champions of the Lega Pro division 1, beating Hellas Verona in the final game of the season 1–0 to guarantee automatic Promotion to Serie B. Madaschi was named in the Lega Pro, team of the year as a centre Bback. Portogruaro-Summaga struggled during the 2010–11 season in Serie B and was relegated back to Lega Pro, Following their relegation Madaschi travelled back to Melbourne, Australia and played for
Melbourne Heart in a largely successful 10 game injury replacement before heading to Asia. On 16 January 2012, Madaschi joined South Korean outfit
Jeju United. At the end of the 2013–14 season Adrian returned home to Perth. Citing a lack of interest from the
A-League, he signed for local club
Perth SC where he went on to make just three appearances before being snapped up by
Newcastle Jets on 6 June 2014. He was reportedly sacked from the club by owner
Nathan Tinkler, following a player revolt midway through the 2014–15 A-League season. On 20 March 2015, he signed for
Western Sydney Wanderers as an injury replacement for
Nick Ward. == International career ==