The trio were on target in the youth team's 4-3 defeat at Solihull Moors as the Pilgrims fell agonisingly short of their first league points of the season.
Gaukroger was on target from the penalty spot before half-time, with Wilkinson and Jackson both striking from open play after the break.
Boston (4-2-3-1): Jake Frestle; James Mallender (Ben Johnson 46), Harry Cranfield, Daniel Fisher, Joe Hardstaff; Finlay Armond, Ashton Taylor; Jamie Gaukroger, Will Jackson, Xander Crashley; Tom Wilkinson.