Carl Fletcher made six changes to the side that overcame Brighton U21’s on penalties in mid-week. The most notable of which saw Sam Ling return to the starting eleven following a spell on the sidelines out injured. Meanwhile, Sam Sargeant was rewarded for his penalty heroics on Wednesday night with another start.
Orient started the tie brightly and were finding a lot of joy down their opposition’s left-hand side with Ling and Jordan Maguire-Drew combining well.
It was a cross from the latter which produced the first chance of the game, the ball in was met by James Brophy who found Craig Clay, but the central midfielder couldn’t make clean contact with the ball and skewed his shot wide.
Maguire-Drew was again involved moments later, this time whipping a free-kick over the wall and forcing a good stop from Maldon ‘keeper Ben McNamara.
The visitors had their first real chance of the game in the 21st minute when Danny Parish drove from just past the half-way line and let fly with his left foot. However, Sargeant was equal to his effort and produced a fine save to tip the ball over for a corner.
Orient had another chance when Louis Dennis broke down the left and stood a ball up at the back-post for Matt Harrold. The centre-forward then headed it back across the face of the goal, but unfortunately there was no one there to meet it.
The O’s continued to create chances down the left and some neat interplay between Maguire-Drew and Brophy saw the latter flash a ball into the danger zone, though it just evaded Dennis.
Parish broke the deadlock for the visitors, cutting inside and finishing low past Sargeant to give his side the lead just before the break.
Orient came close to finding an equaliser almost immediately after the interval. Brophy broke well down the left, riding a couple of challenges, before cutting back for Josh Wright but the ball ended up getting stuck under his feet and the chance fizzled out.
They came even closer in the 63rd minute when Clay played a pass in behind to Brophy who squared it for Maguire-Drew, only for a defender to make a last-ditch tackle to deny a certain goal.
From that same attack, the visitors went up the other end and grabbed a second. Jorome Slew cut inside and curled one into the O’s goal.
That goal proved to spark Orient into life however, and they got one back immediately from the restart. Harrold nodded into the path of substitute, James Dayton and the winger dinked one over the ‘keeper to get his side back in the tie.
They were almost level minutes later when Dayton set up Wright on the edge of the box, but the 30-year-old failed to keep his shot on target.
The O’s continued to be frustrated in their attempts to find a leveller with Wright being denied at point blank range by McNamara, before he drifted a header just wide of the goal.
The visitors were reduced to ten men in the 83rd minute when Parish received his second booking for simulation in the penalty area.
Orient were denied a last gasp leveller in the most dramatic of circumstances when first Harrold then Alabi saw each of their efforts blocked on the goal line by brave Maldon defenders.
Unfortunately, an equaliser wouldn’t come, meaning Maldon & Tiptree secured progression to the next round of the competition.
ORIENT: Sargeant, Ling (Alabi 73”), Coulson, Happe, Widdowson, Clay, Wright, Maguire-Drew, Dennis (Dayton 58”, Gorman 77”), Brophy, Harrold
SUBS: Brill, Ekpiteta, Marsh, Ogie
BOOKED: Harrold 14”, Maguire-Drew 27”
GOALS: Dayton 67”
MALDON & TIPTREE: McNamara, Awotwi (Craknell 62”), Kazeem, Dombaxe, Girdlestone, Gordon (Akins 69”), Parish, Hyde, Hughes, Slew (Coombes 86”), Ngamvoulou
SUBS: O’Reilly, Cracknell, Kaid, Brice-Whiffin
BOOKED: Dombaxe 17”, Awotwi 60”, Parish 66”
SENT OFF: Parish 83”
GOALS: Parish 42”, Slew 65”
Referee: Charles Breakspear
Attendance: 3425 (657)