immediately went into the starting lineup. Despite missing almost a month after incurring a suspension for a red card received at the end of November, Osborne regained his place upon his return and joined the club on a two-and-a-half-year contract for an undisclosed fee on 7 January 2014. He scored his first goal for the Robins against his former club Brentford, in a 3–1 defeat at Griffin Park on 28 January. Osborne remained a regular starter through to the end of the 2013–14 season and finished the campaign with 29 appearances and one goal. 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. On 26 February 2015, Osborne joined League One club Colchester United on loan until the end of the 2014–15 season. He made four appearances before suffering an injury, which led to his recall to Ashton Gate on 4 April 2015. On 2 July 2015, Osborne joined League Two club AFC Wimbledon on a season-long loan. He was a regular pick until his season was ended by a medial ligament injury suffered in training in February 2016. The injury meant that Osborne sat out the Dons' 2016 victorious League Two play-off campaign, though he received a winners' medal. He made 25 appearances during the 2015–16 season and was released by Bristol City in June 2016, when his contract expired. He made 32 appearances and scored one goal during two-and-a-half seasons with the Robins. Plymouth Argyle On 24 June 2016, Osborne joined League Two club Plymouth Argyle on a free transfer. A thigh injury suffered early during the 2016–17 pre-season kept Osborne out until October 2016 and as manager Derek Adams' fourth-choice central defender, he made just two appearances before being released from his contract on 16 January 2017. Kilmarnock Osborne moved to Scotland to join Premiership club Kilmarnock on a two-year contract on 16 January 2017. Five days later, he made his debut versus Hamilton Academical in the Scottish Cup fourth round and conceded a last-minute penalty, which resulted in a 1–0 defeat. Osborne was substituted due to injury in the following match and would