Brophy’s diving header on 68 minutes was enough to see the O’s back to E10 with three points.
Head Coach Justin Edinburugh made one change to the side that defeated AFC Fylde on Saturday, Lamar Reynolds made way for Sam Ling who took a place on the bench for the first time since the FA Cup draw at home to Scunthorpe United on December 5, 2015.
The reverse fixture took place in late November when Macauley Bonne and Jobi McAnuff salvaged a point after goals from James Akintunde and Ross Hannah gave today’s opponents the lead within 40 minutes of play.
A late change in the line-up saw Dan Happe take George Elokobi’s spot in defence while Lamar Reynolds took a seat on the bench as Chester got the game underway.
The hosts gave Dean Brill an early feel of the ball after captain Ryan Astles headed straight in to the hands of the O’s stopper.
Josh Koroma had the first chance for Orient as the winger fired wide of the target after receiving the ball deep in midfield.
Macauley Bonne was next to test the Chester ‘keeper when he capitalised on a mistake in defence but could only shoot in to the hands of stopper Sam Hornby.
Neither side had registered a clear-cut chance at the half hour mark but Brophy had come close after collecting Dan Holman’s pass out wide the winger cut on to his right foot and shot towards goal but the effort didn’t have enough power to trouble Hornby in the Chester net.
The second-half began in similar fashion to the first, neither side were able to create any clear chances as both defences stood firm, Joe Widdowson held off pressure from Craig Mahon while Ryan Astles kept Bonne at bay.
The O’s had to be patient in their football at the hour mark, but Clay kept possesoin well as he looked to unlock the Chester back four.
That was until James Brophy dived at the ball to nod home Jake Caprice’s perfect cross on 68 minutes to give the O’s a 0-1 lead.
When Chester made a double attacking change on 78 minutes their impact was instant as the hosts began to push the O’s deeper and attack the full-backs heavily.
But Koroma sprinted passed his man with ease on the counter and crossed for Bonne whose attempt on goal took the ball over the crossbar in what was a great chance gone begging for Orient.
Debutant Sam Ling came on for Koroma and that chance allowed Caprice to get further forward and the full-back delivered to Bonne at the back post but the striker was just a yard behind the ball as it ran out of play.
Chester again launched the ball in to the box for Harry White but the number nine’s touch let him down as O’s ‘keeper Brill raced out to collect the ball and clear the danger.
Coulson and Dan Happe head clear balls that were lauched in behind the Orient back four as Chester tried to level the scores in the latter stages but resolute defending saw the game end 0-1.
Chester: Hornby, Halls, Astles (C), Mahon (Akintunde 78), Hannah, Hobson, Vose, Crawford, Roberts, Archer (White 66), Anderson (Waters 78).
SUBS: Firth, Dawson
BOOKED: Roberts (12), Mahon (54), Halls (69)
ORIENT: Brill, Caprice, Happe, Coulson, Widdowson, Koroma (Ling 86), Clay, Adams (Lawless 68), Brophy, Bonne, Holman (Harrold 68)
SUBS: Grainger, Reynolds
BOOKED: Adams (13), Brophy (86)
GOALS: Brophy (68)
REFEREE: Matthew Dicicco
ATTENDANCE: 1,935 (245)