Pittman sought his official bid to compete for the host nation at the 2000 Summer Olympics in Sydney, but the match was called off during the AIBA Oceania Qualification Tournament, because of a controversial decision.
[8] Pittman won 3 fights in 3 days to Win the gold medal at the 2003 Commonwealth Championships, beating Eamonn_OKane from Northern Ireland in the final.
Having trained eight years for his Olympic debut in Sydney and missed out, he bounced back to guarantee a spot on the Australian boxing team after finishing first in the AIBA Oceania Qualification Tournament in Tonga.
[11] On 5 April 2008, Pittman faced three-time defending WBA super middleweight champion Felix Sturm in Düsseldorf, Germany.
In early 2010, Pittman's game plan had been overwhelmed with another debacle, after being knocked out by Ghana's Joseph Kwadjo for the IBF Australasian super middleweight title during the seventh round of their match at Le Montage Reception Centre in Sydney.
[14] In 2011, Pittman lost the PABA super middleweight title to fellow Australian boxer Serge Yannick in an unprecedented second round of their match in Hobart, Tasmania.
Two years later, Pittman restored his form in the boxing scene with a clinical shutout over Zac Awad in the eighth round of their match, and ultimately clinched the PABA super middleweight title at the Sydney Entertainment Centre, hastening his pro record to 22–3 (8 KO).
[15] Since fighting professionally, Pittman has been focussed on coaching existing and new Australian talent as part of Team Business[16] working with both elite and pro athletes on the Central Coast (New South Wales), including Kaye Scott and Tyson Lantry.