Macauley Bonne headed the O’s into a sixth minute lead, but Chester were controversially awarded an equaliser when James Akintunde’s effort was deemed to have crossed the line on the 16th minute.
Chester then took the lead from Ross Hannah’s 40th minute free-kick, before Orient defender Jamie Sendles-White was given his marching orders three minutes later after being adjudged to have brought down Nyal Bell in the box.
Sam Sargeant was able to deny Hannah from the spot kick however, guessing correctly before McAnuff strike an unstoppable shot to ensure a point for Orient.
Interim Head Coach Ross Embleton made no changes to the squad that rescued a point at home to Dover on Saturday afternoon.
Orient got the game underway brightly and kicked towards the South Stand this evening, a number of corners meant Joe Widdowson nodded over from just outside the six-yard box.
Six minutes in and the O’s continued to mount the pressure on Chester and took the lead through Macauley Bonne who flicked Jobi McAnuff’s cross over the head of Alex Lynch in the visitors’ net.
After a contained spell of pressure from Chester, Orient seemed to have taken control of the game for James Akintunde’s touch from a cross which the referee bizarrely deemed to have entered the goal, which brought the visitors level.
Despite just conceding the O’s continued to create dangerous chances when Bonne’s lay off to James Dayton allowed the midfielder to unleash a shot but Lynch was equal to it and beat it away from danger.
Moments later, Craig Clay’s goal-bound header from a Dayton corner is deflected inches over the bar still with 25 minutes left of the opening half.
Well against the run of play Chester took the lead through Ross Hannah’s driven free-kick, won just outside of the box, when Akintunde went down dramatically under a challenge from Jamie Sendles-White.
Two minutes later, the visitors were awarded a penalty when a defensive mix-up led to Bell going down under a challenge from Sendles-White, who in turn received a red card for his play.
Sam Sargeant guessed correctly and brilliantly denied Hannah a second goal from the penalty spot.
In a dramatic end to the first half, referee Alan Dale then sent Ross Embleton to the stands for the remainder of the game.
On the stroke of half time Dan Happe had the ball in the back of the net after a lay off from a corner but the referee’s whistle had already blown and the O’s were denied a goal and Chester were awarded a free-kick.
Two changes for the O’s at the break saw Zain Westbrooke and Matt Harrold introduced in place of Alex Lawless and Craig Clay which meant the O’s operated with a 4-3-2 formation.
An early chance for Orient saw James Brophy dart down the left wing and cut the ball inside for Dayton whose deflected effort bounced just wide of the target.
Orient continued to push forward for the equaliser, and with an hour played got their reward.
McAnuff picked up the ball 30-yards from goal and drilled an unstoppable strike past Lynch who stood no chance of reaching the skipper’s excellent effort.
Even with a man disadvantage the O’s looked the more dangerous side. Jake Caprice, Brophy and McAnuff repeatedly charged at the Chester defence but struggled to find a breakthrough.
David Mooney was introduced for the final nine minutes as he came on in place of Dayton, and with 86 minutes on the clock the O’s Club Captain had a chance to become the hero when Harrold’s header back across goal fell to him on the penalty spot, but despite connecting sweetly with the ball his strike whistled wide of the goal.
Despite pushing forward all half, Orient were unable to force a winner and had to settle for a share of the spoils.
ORIENT: Sargeant, Caprice, Sendles-White, Happe, Widdowson, Clay (Harrold 45), Dayton (Mooney 81), Lawless (Westbrooke 45), Brophy, McAnuff (C), Bonne
SUBS: Brill, Ellis
GOALS: Bonne (6), McAnuff (60)
BOOKED: Sendles-White (38), Clay (45+4), Bonne (88)
SENT OFF: Sendles-White (43)
CHESTER: Lynch, Halls, Rowe-Turner (Anderson 77), James, McCombe, Hannah, Bell, Dawson, Akintunde, Gough, Rainey (Slew 81)
SUBS: Vaughan, Jones, Marsh-Hughes
GOALS: Akintunde (16), Hannah (40)
BOOKED: Bell (19), James (90+2)
REFEREE: Alan Dale
ATTENDANCE: 3,352 (173)