Vastly experienced player and a former Welsh International, comfortable in several positions, who joined the Pitmen in May 2025 after a spall at Spalding United
East Midlander Freeman began his career at his boyhood club Nottingham Forest, signing his first professional contract with the club at the start of the 2010-2011 season. His first appearance amongst the first-team ranks came soon after as an unused substitute in a League Cup tie against Bradford City in August 2010, playing mainly in the reserve side for the remainder of the season before agreeing a new contract extension in the summer of 2011
After making his Forest debut early into the 2011-2012 season against Wycombe Wanderers in the League Cup, Freeman was loaned out to Blue Square Premier neighbours Mansfield Town on an emergency loan deal in November 2011, which was extended until January 2012 after an impressive showing from the right back in his first month at Field Mill
Upon his return to the City Ground, new Forest manager Steve Cottrell handed him his first start for the club, with Freeman playing the whole ninety minutes of the FA Cup third-round tie against local rivals Leicester City in January 2012
Another emergency loan was to follow shortly after, as Freeman made the short hop across the Trent to join near-neighbours Notts County in League One for an initial thirty days. A highly impressive loan spell at Meadow Lane saw the loan extended to the end of the season, with Freeman making eighteen starts and being named the Football League's Young Player of the Month for February 2012
His deal at Forest had come to an end in May 2012, with County eager to snap up the youngster on a permanent deal. However, local rivals Derby County beat the Magpies to the signature of the player for an undisclosed fee on a two-year contract. His Championship debut for the Rams came in November 2012 against Blackpool, with games following against Wolves and Bolton before Freeman suffered an ankle injury in the Bolton game that ruled him out for a few weeks
After struggling to get back into Nigel Clough's side, Freeman was loaned back out to Notts County in November 2013, where he made seven appearances in his month back at Meadow Lane. He made a swift return there in January 2014, again making seven starts in a two-month loan spell
Clough had, by this point, departed for Sheffield United as manager and took the opportunity to bring the right-sided player with him on loan in March 2014. He impressed whilst at Bramall Lane and saw his initial one-month loan extended until the end of the current season
Having been frozen out at Derby by new manager Steve McClaren in the build-up to the 2014-2015 season, Freeman was loaned out to Mansfield Town once more in October 2014, making eleven appearances in a three-month spell back at Field Mill. Upon his return to Derby, the two parties agreed to a mutual contract termination in January 2015, allowing Freeman to link up with Clough once more at Sheffield United on a two-and-a-half-year deal
Freeman was to spend the next five years at Bramall Lane, making well over 100 appearances for the Blades as they made their way back from League One to the Premier League in the next four years. Freeman had been used sparingly by new manager Nigel Adkins in the 2015-2016 season and found himself out of favour, joining fallen giants Portsmouth in League Two on loan in January 2016 until the end of the season
Upon his return to South Yorkshire, new Blades manager Chris Wilder immediately transfer-listed Freeman but was to be proven wrong by the player as he became a mainstay in the side that ran away with the League One title in 2016-2017. Freeman was included in the PFA League One Team of the Year, which was enough to convince United to offer him a new contract
A season of consolidation and a mid-table finish in 2017-2018 was followed by a promotion to the Premier League in 2018-2019, with the Blades finishing second in the Championship table behind title winners Norwich City. Freeman made twenty starts this season and was rewarded with a call-up to the full Wales squad in October 2018, making his one and only appearance as a substitute in a friendly against Albania
Game time was to become sparse for the player in the Premier League, with Freeman used mainly as a substitute by Wilder in United's impressive first season back in the top flight. After making four unused substitute appearances, Freeman made his Premier League debut as a substitute in a 3-0 defeat at Newcastle United in June 2020 as the recently-struck Covid pandemic extended the league season beyond its normal May deadline. He followed this up with another appearance at Tottenham a couple of weeks later, sandwiched between a late appearance against Arsenal in the quarter-final of the F.A. Cup
With games continuing behind closed doors for the 2020-2021 season, Freeman once again found himself largely amongst the Blades substitutes as they hit a heavy bout of second-season syndrome in the Premier League, finishing rock bottom of the table at the end of the campaign. Freeman had already departed the club at this point, however, joining League One side Swindon Town on a short-term deal in January 2021 until the end of the season. However, this was to prove to be a very short stay at The County Ground as he was used as part of a deal involving Jordon Garrick in February 2021, which saw Garrick move to Swindon and Freeman step back up to the Championship to join Swansea City
After only one substitute appearance for the Swans, Freeman was on the move once more in July 2021 with a return to Portsmouth, this time on a two-year deal. He was an ever-present for Pompey in the first half of their League One season until an ankle injury sustained in a game against Burton Albion in February 2022 ruled him out for the remainder of the season. The following season saw Freeman only play a handful of times for the club as they finished just outside the play-offs in League One
Freeman dropped into non-league football for the first time in his career in 2023-2024 as he joined fallen giants Oldham Athletic - now in the Vanarama National League - on a short-term deal in August 2023. He made nine starts for the Latics before electing to leave the club upon the expiry of his deal there in January 2024
A return to the National League in August 2024 saw Freeman join Hartlepool United, again on a short-term deal. He was ever-present for Pools in the early part of the campaign but decided to leave in December 2024 to return to the East Midlands with a move to Southern Premier League Central side Spalding United. He was an influential figure at the Sir Halley Stewart Field, playing nineteen times and creating countless chances for his team-mates with his expert set-piece delivery
In May 2025, Freeman was unveiled as the latest big-name capture by the Pitmen, linking up once more with former Sheffield United team-mate Chris Hussey and former Spalding team-mate Tony Breeden at Keys Park ahead of the club's 2025-2026 Northern Premier League campaign