Dimaio was on the books of Stockport County when a storming second half to the 2018-19 campaign saw them transform themselves from also-rans into champions.
Although he spent part of the campaign on loan at Ashton United, the midfielder knows the importance of building confidence through momentum.
"It's massive," he said.
"At Stockport I think we were about 13th coming into Christmas and just went on an unbeaten run.
"Chorley looked favourites that season but we overtook them.
"It's just about confidence in the group. You win one, then two, you think can we win three? Then it gets to 10 games and you're thinking we're pushing now, lets keep focussing."
Stockport finished the season on 82 points, picking up 50 of those in the second half of the campaign.
Amazingly, Boston are currently three points better off after 18 games (28 points) than County were at that stage three seasons ago.
Ex-Sheffield United and Chesterfield player Dimaio - who has been reunited with his old Hatters teammate Scott Duxbury at Boston - believes the Pilgrims have to ability to enjoy a productive second half to the season.
"The talent in this group is probably the best I've been around, and I've played in the Football League," he added.
"We're more than capable of going on a run and climbing the league."
MORE PILGRIMS: Injury setbacks for Jordan Burrow and Jake Wright - news
MORE PILGRIMS: Boston United v Brackley Town - photo gallery
MORE PILGRIMS: Why Boston versus Brackley could not be postponed despite Covid cases - news
MORE PILGRIMS: Elliott refuses to be downbeat, but knows where Boston must improve - news
MORE PILGRIMS: Wilkin praises Saints' battling spirit - news
MORE PILGRIMS: Boston United 1 Brackley Town 3 - report