Over the course of the next few seasons, Boyd`s appearances for the first team were infrequent. He found the net on a regular basis when given the opportunity, but often found himself left out of the side in favour of more established strikers. Successive Pools managers seemed unable to get the best out of Boyd on a consistent basis. In 2003/04 he seemed to be on his way out of the club when Neale Cooper allowed him to join third division Boston United for a loan spell. Boston were keen to make the move a permanent one but they lacked the funds to pay a transfer fee. Their loss was Pools` gain as Boyd returned home and produced a dazzling end to the season, scoring 12 times in the last ten games as Pools surged from midtable to the play-offs.
The following season saw Boyd finally establish himself as first-choice striker and with the security of a first team place his form and confidence were sky-high. His creative forward play helped to create numerous goals for other players and he weighed in with 29 himself, including a wonderful hat-trick against Sheffield Wednesday. Boyd signed an extension to his Pools contract in 2005, but the season that followed was a bad one for both player and club. Boyd injured his knee early in the season and his recovery was delayed when the knee became infected after surgery. He missed five months of the season and, although he did return to the side, he couldn`t provide the spark to save the club from relegation.
Former Pools manager Mike Newell, who was unsuccessful in an earlier attempt to prise Boyd away from Pools, returned in the summer of 2006 and this time his offer was accepted by the club and Boyd was transferred to Luton Town in July 2006. Boyd had an unhappy time at Kenilworth Road and he made just a handful of first team starts in his year at the Hatters. He moved on to Leyton Orient where he rediscovered some of his old form, scoring 29 goals in his two seasons including a winner against Pools at Brisbane Road in November 2008.
Boyd returned to Hartlepool for a second spell in May 2009. Sadly, the striker was unable to capture the heights of his first spell. He added 19 more goals to his Pools tally, taking him to joint seventh on the all-time list, but he was a largely peripheral figure during his three seasons. A brief flicker of the old fire saw him start the 2011/12 campaign in good form, but he drifted from the first team scene, and started just once in the second half of the season. He was released in May 2012, just a couple of weeks short of his 30th birthday.