Bourne Town slipped to a fourth successive away defeat as derby-day rivals Oakham United returned to the top of the table on Wednesday night.
The Wakes went ahead after just two minutes through top scorer Zak Munton who then put them back on level terms following strikes by Alex Brockbank and Edward McDonald.
Michael Nelson made it 3-2 before the break, only for Craig Rook to equalise from the penalty spot.
Goals in the final six minutes from McDonald and Ben Easson (penalty) earned the points for Oakham.
CHROMASPORT & TROPHIES UNITED COUNTIES LEAGUE
Knockout Cup second round: Boston 0 Holbeach 2 (Holbeach at home to Eynesbury, Olney or Rushden & Higham).
Division One: Oakham 5 Bourne 3.
Reserve Division: Desborough 3 Blackstones 1, Harborough 1 Whitworth 3, Thrapston 2 Peterborough Northern Star 5.