Crewe Alexandra scored a 90th-minute winner in a 2-1 win at Brisbane Road which left Orient fans fuming at their defence.
After enjoying a great start to the game, The O’s fell behind after Eddie Nolan poked Crewe ahead at the half-hour mark, a lead that would only last ten minutes.
Orient’s Maguire-Drew levelled the tie after intercepting the ball in a dangerous area before finishing the move with a delicate dink which saw the two sides go into the break level.
After the break, The O’s came out fighting and just after the 55-minute mark were awarded with a penalty after a trip on Josh Wright by Crewe’s Nicky Hunt.
Maguire-Drew failed to net the penalty and from there onwards the tie looked set to be in Crewe’s favour.
Super goalkeeping from Dean Brill denied a goal for Crewe in the 80th minute, making a brilliant double save for what looked certain to be the winner.
The game saw its winning goal right at the death as an Owen Dale cross deflected kindly to James Jones on the edge of the area who then smashed home the winner.
The late goal came after The O’s conceded a late penalty last Saturday against Exeter as well as a late own goal against Salford towards the end of August.
Orient fans were left feeling disappointed after dropping points to yet another late goal:
Been coming for the last ten minutes, shocking, shocking, shocking loss. #lofc
— Daniel Auton (@DanAuton2590) September 17, 2019
What happens when you miss a penalty. 3 points dropped. Need to sort the defence out. Giving ourselves uphill battles to climb.
— Sebastian Cain (@SebCain) September 17, 2019
— Scottie 56 (@elmojon7) September 17, 2019
Missing pens and shocking defending. Is it any wonder we lost?
— 🍩 Andy 🍩 (@OrientMeatPie) September 17, 2019
Oh no, we need to get on it now. No more drama please.
— Orient44 (@Orient441) September 17, 2019