Freeman was a regular for the reserves in the 2010–11 season, and he was named as a substitute by Billy Davies in a Football League Cup first round match with Bradford City in August 2010.

[3] Freeman made his first professional appearance for Forest on 22 August 2011 in the second round of the League Cup during a 4–1 victory over Wycombe Wanderers, coming on for Lewis McGugan.

[10][11] Under Steve Cotterill, Freeman was given his first start for Forest, in an FA Cup third round tie at home to rival club Leicester City in January 2012.

He was also praised the current Notts County manager, Keith Curle, who stated that in the future Freeman would be good enough to play in the Premier League.

[25] On 22 August 2012, Freeman joined East Midlands rivals Derby County for an undisclosed fee, signing a two-year contract with an option of a third.

[32] After the sale of first choice right-back John Brayford to Cardiff City, Nigel Clough thought Freeman would be capable replacement.

[33] A couple of days later, Derby signed Tottenham Hotspur right-back Adam Smith on a season-long loan with the intention of the two competing for a place in the starting eleven.

The Rams were 2–0 down at the time and Freeman was at fault for both goals, particularly the second, when he headed the ball into the path of Burnley striker Sam Vokes, who scored from close range.

[36] Smith kept his place in the team for the following two matches but Freeman returned for the third, a 2–1 League Cup defeat to rivals Leicester City.

[43] On 23 January 2015, after being released by Derby County, Freeman joined former loan club Sheffield United on a free transfer signing a two-and-a-half-year contract with the Blades.

During Adkins' tenure as Bramall Lane boss, Freeman found himself "out of favour",[46] and on 28 January 2016 he signed on loan for League Two club Portsmouth for the remainder of the 2015–16 season.

[46] However, Freeman worked his way into the team, becoming "a mainstay of United's starting eleven" as he helped the South Yorkshire side lift the League One trophy, earning with it promotion.

[46] On 31 December 2016, in a home game against Northampton Town, Freeman scored the last minute winning goal which took United to the top of the league, where they were to remain for the rest of the season.

[46] Freeman credited former Foresters Morgan, Jermaine Jenas and fellow full-back Stuart Pearce as some of his favourite players growing up.