Bossy, footy icon Campbell Brown and NRL legend Mick Crocker head off to the Alice Springs Cup in the capital of the Outback.

Bossy and his favourite Irishman, AFL icon Tadhg Kennelly, head out to Victoria to check out its oldest race, the Apsley Cup, established in 1855.

Bossy, AFL icon Campbell Brown and comedian Lawrence Mooney head off to the race at the Elwick Racecourse in Tasmania. Foggy conditions dampen their arrival a bit, but the boys are hopeful the conditions will improve.

Bossy, Lawrence Mooney and Mick Crocker visit the town of Nyngan in rural NSW to check out the Duck Creek Picnic Races.

Bossy takes Tadhg Kennelly and Campbell Brown to the Eastern Wheatbelt in WA for the Kulin Bush Races and they try their hand at farming.

Bossy, Tydhg and Browny are still at The Kulin Bush Races; Bossy returns to the saddle as clerk of the course; Browny rides a bucking bull.