Romy Boco’s debut goal and a late effort from Eoin Doyle ensured the Spireites got off to a winning start back in League One despite former Blade Darius Henderson pulling one back seven minutes from time.
Kevin Lisbie got free behind the Spireites back line after an error but his shot was charged down by Dan Jones.
Jones crossed in well ahead of Gary Roberts stabbed pass towards Eoin Doyle, but neither ball in reached its intended target.
The Spireites took the lead on seven minutes. Jimmy Ryan’s shot blocked by Mathieu Baudry but the ball almost stopped dead and Boco pounced, at full stretch, to score from an angled 10 yard shot on his debut.
Doyle took advantage of some hesitation by the Orient defence, he robbed Elliot Omozusi, raced forwards but his shot hit the upright.
Tommy Lee had to get down quickly to his left to keep out a David Mooney shot and seconds later he had to make a double save to deny Dean Cox and Lisbie.
The game’s first corner saw Ritchie Humphreys get on the ball but his effort was simple for Adam Legzdins.
Baudry booked for a foul and Roberts 30 yarder from the resulting free kick was simple for Legzdins but the keeper was pleased to see a Roberts shot fly wide after clipping Doyle.
Lisbie headed a Cox free-kick just over the bar as Orient continued to play with freedom but they were just unable to get the better of a back line led masterfully by Ian Evatt.
Lee juggled with a long throw from Nathan Clarke and, under pressure from Lloyd James, dropped it, the ball fell to Lisbie, two yards out, but he hit the ball straight into Lee’s grateful arms.
Evatt had a fine chance to double the lead early in the second half, but he headed over from six yards from an inch perfect Dan Jones header following a quick Roberts free-kick.
Shane Lowry hit well over from range as the O’s tried to string some passing together, but it was the visitors who were bossing the early second half phases.
Legzdins had to make a superb save to deny Doyle after Roberts had robbed his former Huddersfield team mate Clarke. The striker hesitated just a fraction of a second before releasing his shot allowing the keeper to position himself well and dive right to save.
Orient earned back to back corners, their first of the game but Chesterfield defended them well, though the double flag-kick lifted the home fans.
New signings Jay Simpson and Jobi McAnuff came on with 58 played for Lisbie and Bradley Pritchard and McAnuff headed just wide from a Cox cross with his first touch.
Jay Simpson’s shot deflected for a corner that led to a quick break from the Spireites, Ryan’s cross was just taken off Doyle’s head by Elliott Omozusi.
Henderson became Orient’s third debut making sub, replacing Mooney.
Baudry escaped a second yellow and Evatt headed well wide from Roberts’ subsequent free-kick.
Clarke was carded for pulling back Doyle as he looked set to break-through, the blue shirts were calling for a red card for the red shirted defender. Roberts hit just over from 20 yards.
Chesterfield were in dreamland on 77 minutes when the lead was doubled.
Evatt’s chip forward found Doyle who had to wait seemingly an age for the ball to come to heel before he lifted it over the keeper to seemingly win the game.
Leyton Orient hit back seven minutes from time. Boco was yellow carded and from the free-kick Cox’s low shot was blocked by Lee and Henderson popped home the loose ball from a yard.
Chesterfield had no real anxious moments in the final exchanges which included four additional minutes to ensure the points were theirs.
Chesterfield manager Paul Cook was dealt a blow in training yesterday when his intended lone front man, big Frenchman Armand Gnanduillet, went over on his ankle and was forced to miss the trip to East London.
So last season’s top scorer Eoin Doyle started against the side that lost to Rotherham United on penalties in the Wembley play-off final last May.
The manager handed debuts to former Owl Dan Jones at left-back and last-minute non-contract signing Romy Boco, a regular Cook player having had three spells alongside him at Sligo Rovers and two at Accrington Stanley.
Three of Spireites’ subs have never managed a Football League appearance whilst Ollie Banks and Jay O’Shea are both short of full fitness.
Russell Slade’s O’s have seen Moses Odubajo move across London to Brentford for £1m this summer but he has brought in former Blades striker Darius Henderson, former Doncaster keeper Gary Woods and Reading’s Jobi McAnuff but they were all on a very strong bench for a team Paul Cook has cited as favourites for the title.
Debut maker Romy Boco made a great start for his new club. A good passing move saw Jimmy Ryan shoot from range, his effort was blocked by Mathieu Baudry but the ball fell for Boco, at full stretch, the stab home from an angled 10 yard shot.
Orient (4-4-2): Legzdins, Omozusi, Baudry, Clarke, Pritchard, Cox, James, Lowry, Vincelot, Lisbie, Mooney. Subs: Woods, Sawyer, McAnuff, Batt, Bartley, Henderson, Simpson.
Chesterfield (4-2-3-1): Lee, Darikwa, Evatt, Cooper, Jones, Morsy, Ryan, Boco, Roberts, Humphreys, Doyle. Subs: Chapman, Hird, O’Shea, Raglan, Dawes, Banks, Johnson.
Ref: Michael Bull (Essex).
Attendance: 5,619 (841 away)