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Grimsby Town's initial bids were rejected by Solihull, due to falling below Solihull's valuation. However, on 18 January 2017, Osborne signed a ​2  ⁄2 -year deal with the newly promoted League Two side for an undisclosed fee. He made his professional debut with Grimsby in the 2–0 home win over Notts County; he provided the assist for the opening goal, his initial cross turned away, then from the byline Osborne cut the ball across the penalty area for Omar Bogle to turn home; Osborne was also involved in the buildup to the second goal, placing a through ball to Bogle on the right hand side of the box, with the goalkeeper deflecting into the path of Scott Vernon who slotted home from an acute angle. His performance earning him the Man of the Match award and he was also named in Sky Bets EFL: Team of the Week for the month of January 2017.

In July 2017, Osborne ruptured his posterior cruciate ligament, ruling him out for the next five months. On 8 November 2017, Osborne made his comeback in a 1–1 draw against Sunderland U21s in the EFL Trophy.

On 1 December 2017, Osborne rejoined Solihull Moors on a 28-day loan. He signed on a permanent deal on 8 January 2018, for an undisclosed fee.

Despite attracting League Two interest from the likes of Crawley Town, Notts County and Crewe Alexandra where he spent time training towards the end of last season but suffered a dislocated shoulder injury; he moved to Southern League Premier Division side Redditch United for the duration of the 2015–2016 season. An approach by former Hednesford manager Rob Smith at AFC Telford United was made in February 2016, however, he decided to stay at Redditch who were mounting a promotion bid from the Southern Premier League. On 25 January 2016, he scored the winning goal in the quarter-final of the Birmingham Senior Cup, a 20-yard strike in the 63rd minute from the left-hand corner of the area flew into the far top corner.

The following season in May 2016, he moved to newly promoted National League side Solihull Moors. Before the season started however, he had another trial at Crewe. He scored a brace in the FA Cup second round against Luton Town; in the first five minutes turning on the edge of the box and curled a strike into the top corner, his second came on 35 minutes, good work at the byline by Akwasi Asante who was able pick out a pass to Osborne free at edge of the box who fired a low shot into the bottom corner.

Osborne was born in Solihull, West Midlands. He began his career with Hednesford Town as a member of the club's youth system in the under-18s team. He scored on his full debut in a 3–0 win at Didcot Town, running at pace took him away from his marker, making just enough space for him to strike a breathtaking curling shot from fully thirty yards that swerved past the goalkeeper and into the top far corner of the net.

Osborne joined Evo-Stik Division One Rushall Olympic on a month's loan in February 2011. He was part of the Hednesford side that were promoted in the play-off final 2–1 victory over F.C. United of Manchester, Osborne scoring what turned out to the winning goal. He was part of the team that won the Staffordshire Senior Cup trophy in April 2013 for the first time since 1974, with a man of the match performance in the final, scoring two goals in five minutes after the hour mark in their 5–1 victory over Rushall Olympic. His performances over the 2013–2014 season rewarded him with the Supporters Player of the Year award.

A skillful, creative box-to-box midfielder, he is known for his good passing and technical ability as a playmaker. Osborne began his career at Hednesford Town in 2008 where he started as a youngster and established himself in the "Pitmen's" first team in the 2009–10 season, he spent the next ​4  ⁄2 years there. He then joined Redditch United in 2015 before moving to his hometown club Solihull Moors for the start of the 2016–2017 season.

Jamey Osborne (born 7 June 1992) is an English footballer who plays as a midfielder for National League side Solihull Moors.