Following 10 successive league victories over the Cumbrian outfit, United were edged out in a tight encounter which Workington won courtesy of strikes in the final 10 minutes from Jonny Wright and Gareth Arnison.
Spencer Weir-Daley had earlier equalised Arnison’s spot-kick, but the Reds prevailed as chances went untaken at both ends.
The Pilgrims had fielded a particularly youthful XI for the visit of Workington, with teenagers Jason Field and James Reed handed starts in place of injured duo Gareth Jelleyman and Matt Wilson.
Korey Dyer-Stewart was also included on the bench after signing senior forms on Thursday evening.
United started well and Mark Jones fired an early effort wide following Marc Newsham’s left-wing assist.
Jones was involved again when he headed down Field’s raking cross and Weir-Daley’s curling effort was touched aside by Aaran Taylor.
Newsham was then denied by an impressive stop from Taylor as United continued to make all of the early running.
The Reds took the lead against the run of play on 14 minutes. Gary Silk fouled Andre Rodrigues Da Costa inside the box and ARNISON drove home the spot-kick despite Dan Haystead getting a strong hand to the ball.
United continued to play decent football and eventually found a breakthrough seven minutes before half-time. Jones laid the ball through for WEIR-DALEY to steady himself and dispatch a low finish beyond the despairing dive of Taylor.
Taylor clutched a stinging drive from the advancing Field on the stroke of half-time, while Haystead did well to deal with Mark Boyd’s audacious 30-yard free-kick.
Dyer-Stewart was introduced at half-time with Jones withdrawn through injury and the teenage substitute almost had an immediate impact. Winning the ball off Gari Rowntree in a ferocious challenge, he advanced into the box before being well denied by keeper Taylor.
Weir-Daley then headed over the bar following an Ian Ross corner.
The Pilgrims were presented with a glorious opportunity to get their noses in front when Kern Miller clipped the ball through for the usually-reliable Newsham — but the striker’s firm drive came back off the post.
Workington took full advantage. Substitute Jordan Connerton skipped round the challenge of Silk to tee up WRIGHT to drill the ball home from close-range.
Boyd fired another drive fractionally wide before the Reds wrapped up the points with ARNISON driving a firm effort beyond Haystead from 18 yards.
There was still time for Taylor to deny Ross from a 25-yard free-kick, but the Pilgrims already knew their fate.
Boston (4-3-3): Dan Haystead; Gary Silk, Kern Miller, Nathan Stainfield, Jason Field; Ben Milnes, Ian Ross, James Reed (Kallum Smith 80); Spencer Weir-Daley (Ben Fairclough 73), Mark Jones (Korey Dyer-Stewart 46), Marc Newsham. Subs (not used): Jason Stokes, Tom Ward.
Workington (4-4-2): Aaran Taylor; Niall Cowperthwaite, Kyle May, James Bolton, Gari Rowntree; Will Vaulks (Phil McLuckie 67), Mark Boyd, David Hewson, Andre Rodrigues Da Costa (Jordan Connerton 73); Jonny Wright (Chris Wraighte 86), Gareth Arnison. Subs (not used): Jake Simpson, Josh Todd.
Referee: Neil Hair