The Gladiators trailed 18-8 at half time and fell further behind immediately after the restart before staging an almighty fight back to wrap up a memorable 30-24 win.
Chester were well below par in the opening 40 minutes and the clinical visitors took advantage of some slack defence to open up an early 12-0 lead.
Bolton's speed around the ruck caused the Gladiators plenty of problems early on and it took until the 20 minute mark for Chester to settle into the game.
Chris Pape forced his way over the whitewash to get the Gladiators off the mark but Chris Smith was off target with the boot.
Some more weak defence saw Bolton extend their lead to 18-4 before Smith reduced the arrears by crossing in the corner although his conversion attempt fell short.
Chester headed into the break trailing 18-8 and things failed to improve at the start of the second period.
Bolton's first attacking foray saw the Mets score an excellent long range try and take a commanding 24-8 lead.
However, the Gladiators responded well with prop Andy Hill crashing over for a try on 50 minutes and Smith's conversion cutting the visitors advantage to 10 points.
Fullback George Bryant then touched down a Pape kick as Chester moved to within six points and began to sense the momentum was shifting.
The Gladiators levelled matters on 65 minutes thanks to stand-in hooker Chris Maloney's try and Smith's conversion.
Just five minutes later, Chester took the lead for the first time in the match when winger Mark Hanson streaked down the left wing and touched down under the posts with Smith adding the extra to put the Gladiators 30-24 in front.
Bolton pushed forward in the final 10 minutes in search of a way back into the game but some resolute Gladiators defence saw the home side through and ensured Chester claimed the points.