Boyd started his career as a centre-back for St Francis, a local Sunday League team in Hartlepool. He was spotted by scouts and offered a contract at Hartlepool United. Boyd first gained recognition as a 17 year old after scoring a dramatic last minute goal against Shrewsbury from the tightest of angles on his debut. However Boyd’s early promise quickly faded as the youngster found himself languishing in the reserves and struggling to make an impact. From the seasons 1999-00 to 2003 Boyd had started a total of 25 first team matches and made 38 substitute appearances. Despite this, Boyd had only managed to score 15 goals.

Boyd’s lack of first team appearances prompted Hartlepool manager Neale Cooper to loan him to Boston United in order to gain match practice. During his time at Boston, Boyd won critical acclaim from Boston manager Neil Thompson and played a total of 14 matches scoring 4 goals before returning to Hartlepool. Boyd returned 9lb over weight and looked set to leave Hartlepool United after angering Cooper. When asked about his weight gain. Boyd claimed that he had been eating more to build up his strength but when asked about gym work he said he had not started it yet. Boston looked set to make permanent deal for Boyd and made an offer for the striker. However the two sides failed to reach an agreement with Boston claiming that Hartlepool were asking for far too much. It was rumoured that Hartlepool chairman, Ken Hodcroft, wanted a six figure sum, which at the time seemed steep for an unproven striker and it was thought that Boston were only prepared to pay a four figure sum of around £5,000.

Boyd was then a surprise inclusion in the team to face Stockport and came on as a sub after 45 minutes. The next game away at to Grimsby saw Boyd get his first start of the season for Pools and score two goals. Boyd kept his place in the team and continued to score for the remainder of the season and notched an impressive 12 goals in 12 starts. Neale Cooper noticed a change in Boyd's attitude and commitment to the club and made Boyd Hartlepool's first choice striker.

The following season Boyd became one of the most feared strikers in League 1 and formed a strong partnership with fellow striker Joel Porter. He scored 29 goals in league and cup and became the club’s highest goalscorer since Joe Allon in 1991. The pick of Boyd’s goals came against Sheffield Wednesday where Boyd received the ball outside the box and faked his way past two players before chipping a lovely effort over Sheffield Wednesday keeper Gallacher. This goal earned him two awards, Hartlepool United's Goal of the Season 2005 and the North East Goal of the Season 2005. To top that off Boyd was also named Hartlepool United’s Players’ Player of the Year. Boyd ended the season strongly and scored a brace in the first leg of the play-off semi final match against Tranmere, which helped to secure Hartlepool’s place in the play-off final for the first time in the club’s history.

As Boyd gained critical acclaim, his value rocketed to £1 million and he attracted the attention of clubs such as Newcastle, Liverpool, Middlesborough and Sunderland. However Boyd remained at the club for the start of the 2006 campaign. Boyd started the season by scoring 2 goals in 4 starts. Unfortunately, Boyd picked up a long-term injury against Yeovil after bruising his bone. To make matters worse Boyd’s injury became infected, which prolonged his return. Former manager, Mike Newell, sought to take advantage of the effect that his injury had lowered his valuation and made Hartlepool two offers thought to be in the region of £500,000. However, Hartlepool rejected these offers. Boyd returned to the first team 4 and a half months later.

Boyd has also become famous for his antics off the pitch after the ex-boyfriend of a woman he was in bed with caught them and assaulted him. Boyd was then forced to flee naked down a posh estate and suffered bruises and injuries to his feet. Boyd refused to take any legal action against his attacker, claiming that he just wants to "forget about it".