Osborne handed the Pilgrims a sixth minute lead against Newcastle United’s under-21s, only for Ben Parkinson to score twice for the Magpies before the break.
Aderoju restored parity in the 76th minute and Maguire won it nine minutes from time.
Manager Graham Coughlan made six changes to his team ahead of kick-off, continuing his efforts to see as many members of his squad in action as possible.
The Pilgrims were rewarded for a bright start with OSBORNE winning back possession high up and the pitch and sailing home a dipping, angled effort from 25 yards.
Visiting keeper Aidan Harris made an excellent save to deny Pemi Aderoju as United sensed a second, but the Magpies levelled in the 14th minute when Alfie Harrison's low drive was deflected home by PARKINSON.
Tony Weston subsequently cracked the post with a low drive, before Martin Woods limped off with a tweak to his calf, having only returned to competitive action days earlier at Ebbsfleet United.
Osborne and Tom Leak were both denied by Harris before the break, with Newcastle edging in front when PARKINSON slammed home from the edge of the penalty area after meeting Darren Palmer's assist.
The game remained open after half-time, with the hosts eventually equalising 14 minutes from time when substitute Maguire crossed from the left and ADEROJU applied the finishing touch from close-range.
Fellow sub Adam Marriott played the role of provider five minutes later - firing the ball across for MAGUIRE to bundle home at the back post to re-assert United's lead.
Boston (4-1-2-1-2): Aidan Stone; Kieran Coates (Jacob Scott 76), Jai Rowe, Tom Leak, Cameron Green; Martin Woods (Jordan Richards 34); Keaton Ward, Sam Osborne (Frankie Maguire 62); Tony Weston (Billy Chadwick 46); Pemi Aderoju, Jacob Hazel (Adam Marriott 62). Subs (not used): Dylan Hill, Jake Lovelace (gk).
Newcastle (4-4-2): Aidan Harris; Leo Shahar (Harry Powell 69), Cathal Heffernan, Charlie McArthur, Alex Murphy; Darren Palmer (James Huntley 77), Lewis Miley, Isaac Hayden (Scott Bailey 62), Johnny Emerson (Josh Donaldson 62); Ben Parkinson, Alfie Harrison (Mohamedou Sedibeh 77). Subs (not used): Ellis Stanton, James Taylor (gk).
Referee: Michael Crusham.
Attendance: 386.
PIC: Russell Dossett.