 He umpired his 350th AFL game in Round 4, 2017, in a match between GWS and Port Adelaide.Rosebury commenced his umpiring career with the South Suburban Junior Football Umpires Association (SSJFUA) in Western Australia, and umpired his first match in the West Australian Football League (WAFL) at only 18 years of age, which is believed to be a record for the youngest officiating umpire in that league.He umpired the 1999 and 2000 WAFL Grand Finals.