Adrian Clifton’s second half strike saw the visitors take all three points away from E10.
Orient got the game underway and immediately attacked Maidenhead who looked shocked at the quick start.
Charlie Lee headed just wide following successive Jobi McAnuff corners for the O’s. Moments later, debutant Jay simpson and Joe Widdowson linked-up well on the left before the latter’s cross was volleyed inches wide of the near post by the late arriving Sam Ling.
The game finally settled down after the thrilling start and Maidenhead had their first decent chance of the game when Adrian Clifton attempted to bicycle kick the ball in to the back of the net following an O’s clearance.
The Magpies went close again after 25 minutes, Clifton was in the box after the O’s failed to clear a corner but the visiting man sliced the ball wide from close range.
Eight minutes of the half remained when James Brophy linked-up with Ling on the right before the latter drilled a low cross towards Macauley Bonne but our striker’s touch took the ball just out of the path of Charlie Lee at the back post.
Simpson tested Carl Pentney in the visiting net just before the break when the ball dropped to the new-signing six-yards from the goal, however his first time left footed effort was well parried by the ‘keeper.
Maidenhead took the lead after 53 minutes when the visitor’s danger man Clifton stroked the ball into the back of the net following a deep cross from Sam Nombe.
Soon after the opener, the visitors broke clear on the right of midfield, Nombe led the charge but his low strike was held well by Brill.
Just under ten minutes remained when newly introduced Dale Gorman picked up Ling’s pass, cut back on to his favoured foot and struck at goal but Pentney was equal to the effort.
Orient were on the hunt for an equaliser when Craig clay advanced into the box and cut the ball back to Harrold who couldn’t control the cross and lifted the ball over the bar from close range.
Almost immediately, Maidenhead broke clear and saw Nana Owusu clip the post from range as he attempted to lift the ball over the run of Brill.
Another chance for the Magpies saw Josh Kelly drag his shot beyond the far post after the visitors attacked the O’s on the counter from the right wing.
That proved to be the final opportunity of the day as the O’s fell to defeat in E10.
ORIENT: Brill, Ling, Turley (Harrold 74), Happe, Widdowson, Brophy, Clay, Lee (Maguire-Drew 71), McAnuff (C), Bonne, Simpson, (Gorman 78)
SUBS: Sargeant, Ekpiteta
BOOKED: Brill (40), Clay (67), Widdowson (90+2), Ling (90+3)
MAIDENHEAD: Pentney, Clerima, Steer, Obileye, Kilgour, Comley, Clifton (Fondop 72), Akintunde (Owusu 75), Upward, Massey, Nombe (Kelly 90+3)
SUBS: Bird, Mason
GOALS: Clifton (53)
BOOKED: Obileye (32), Upward (90+2), Fondop (90+3)
REFEREE: Simon Mather
ATTENDANCE: 5,337 (224)