Chester pushed second-placed Woolston all the way and with some more composure and luck could have claimed the points.
Tries from Dan Rowett, Andy Hill, Mark Carroll, Chris Pape and Paul Foster were supplemented by two Chris Smith conversions but the Warrington-based side held on for the win.
Chester started the game brightly but fell behind on eight minutes after conceding two penalties in succession.
Rowett crossed from close range to level the scores five minutes later but Woolston moved back into the lead almost immediately.
Winger Carroll finished well in the corner to restore parity and prop Hill reacted well to collect and loose ball and reach out to put the Gladiators in front.
Woolston hit back with two tries but half back Pape powered his way over the line on the stroke of half time to send Chester into the break trailing by four points.
Some individual errors and ill discipline gave Woolston the opportunity to move further in front but the Gladiators continued to push foward with veteran Foster crossing for his first try of the season.
Chester spurned several chances to close the gap late on but will take heart from another encouraging performance against one of the promotion favourites.
This weekend the Gladiators travel to Bury Broncos.