Guernsey FC were cruising at 4-0 early in the second half, but two quick Chipstead goals put the pressure right back on.
Such was their dominance in the opening 45 minutes, Josh Addison did not have a save to make.
Midway through the first half, they were gifted the opening goal when Chipstead’s Danial Vaughan diverted a cross into his own net.
Three minutes later Wallbridge was barged over for a penalty which was dispatched by Ross Allen.
As the game reached half time Guernsey FC made it three when Charlton Gauvain’s early shot found the corner. It was his fourth goal in as many games.
The Green Lions continued to carve out chances early in the second half.
Allen made it 4-0 on 52 minutes with a first time shot into the roof of the net.
Daniel Berry and then Jordy Ndzoid scored in quick succession for Chipstead to make things nervy for the home side.
But they soaked up the pressure and with 10 minutes left Matt Loaring made the game safe.
A very late penalty for Chipstead, scored by Leahy, left the final result at 5-3.
Guernsey FC are now sitting in 16th.
Other Isthmian South midweek results: Ascot United 2-2 Ashford Town, Badshot Lea 1-3 Hartley Wintney, Binfield 2-3 Westfield, Chertsey Town 2-1 Leatherhead, Marlow 4-1 Northwood, Raynes Park Vale 2-0 Corinthian-Casuals, Southall 4-1 Hanworth Villa, Sutton Common Rovers 3-0 South Park Reigate.
Guernsey FC: 1 Josh ADDISON; 2 Ben SOLWAY; 3 Jamie DODD (c); 4 Dave RIHOY; 5 Tom VAUDIN; 6 Kieran MAHON (17 Brandon WALLACE, 66’); 7 Charlton GAUVAIN (12 Simon ARNOLD, 90’); 8 Seb VANCE; 9 Owen WALLBRIDGE; 10 Ross ALLEN; 11 Matt LOARING (15 Jacques CAUVIN, 89’). Not used: 13 Christian POVALL.
Booked: Mahon, Gauvain, Allen, Loaring.
Chipstead: 1 Harrison FIRTH; 2 Jaden EDWARDS; 3 Alfie YOUNG (14 Khalid BIBIKIR, HT); 4 Daniel VAUGHAN; 5 Syed Zohair IRTIZA-ALI; 6 Nathaniel KENLOCK; 7 Jack LEAHY; 8 Jordy Ndozid (12 Campbell SCOTT, 84’); 9 Jacob SEWELL (15 Daniel BERRY, 64’); 10 Bradley WILSON (c); 11 Danyaal IQBAL. Not used: 16 Matthew MALES.