After suffering a "horrific injury" to his shin during the 2014–15 pre-season, Osborne returned to fitness in mid-August 2014, but thereafter was entirely out of favour with manager Steve Cotterill and made just three appearances during the club's League One title-winning season, though he did receive a promotion medal. He did not feature at all in the club's Football League Trophy-winning campaign. Osborne spent the entire 2015–16 season away on loan and was released in June 2016, when his contract expired. He made 32 appearances and scored one goal during two-and-a-half seasons with the Robins.