Boland played a key role in the club`s turnaround in fortunes during the 2006/07 season and played in every one of the club record nine consecutive league wins. An injury picked shortly afterwards meant that Boland missed the next three months, and the remainder of his Pools career would be punctuated by a series of other injuries, some more serious than others. He managed 36 appearances during 2007/08 though more often than not he did not complete the full 90 minutes. The season that followed was a near write-off. In the opening game against Colchester he produced a great display, and even scored his only goal for the club with a superb strike from 20 yards. Just two weeks later he was injured against Stockport County, and that was it.
At the end of the 2008/09 season the club announced that they would monitor the midfielder`s condition over the summer before deciding whether to offer him a new contract. It was not to be. On 21st October 2009, 14 months after his last action in a Pools shirt, Boland announced his retirement from the game.