(Photo Courtesy of Jemma Phillips Photography)
An error by goalkeeper Tom Lovelock was pounced upon by Tashan Adeyinka to put the home side in front after just 10 minutes.
City would go on to create a number of chances in front of goal but only efforts from Lee Sawyer and one from Michael Cheek would force Ashley Timms into action.
Chelmsford continued to create opportunities in the second half but were punished for their profligacy when Dave Tarpey added a second, heading in the rebound from a Danny Green shot.
The result was City’s second away defeat in a row following defeat to Concord Rangers in midweek, and their eighth defeat in their last 10 away trips in league and cup.
It was also the first time since November 17th that City had failed to score in a match, despite creating enough goal scoring chances to win three games.
Coming off the back of their defeat in the Essex Derby, Mark Hawkes made two changes to his starting line up with Jaanai Gordon returning to start in place of Leon Redwood and Harry Hickford replacing the suspended Mark Haines.
Chelmsford almost got off to the perfect start when on-loan Southend United midfielder, Jack Bridge struck a first time shot from the edge of the area which was well tipped over by Ashley Timms in the Maidenhead net.
But whilst Timms was excelling at one end, City's custodian, Tom Lovelock had a moment to forget as the hosts took the lead in fortuitous circumstances.
A speculative shot from Eddie Hutchinson nipped up and bounced off the chest of the recently signed Lovelock, falling perfectly into the path of Tashan Adeyinka to stroke home the opener after just 10 minutes.
Once more Mark Hawkes' men had let an early goal slip, but just like Tuesday at Concord the Clarets reacted well creating a number of chances to level matters.
Joe Ward was finding joy down the right wing and he was first to try his luck, skinning Sam Barratt before seeing his effort blocked by Leon Solomon. The teenager would then fail to keep his next attempt under the cross bar after receiving a low ball from Jaanai Gordon.
City would continue to press and Michael Cheek will feel he should have done better after Gordon was played in. After being sandwiched between two defenders the ball squirmed out into the path of Cheek who could only hit it straight at Timms for a comfortable save.
And as half time approached Lee Sawyer had the best chance for Chelmsford to equalise when his barrelling run through the middle was picked out by Bridge, but the midfielder couldn't beat Timms one-on-one.
The second half was more of the same from the visitors who were on numerous occasions getting into dangerous areas, but were either too afraid to pull the trigger or, when they did, find a defender there to block their shots.
Ward was guilty early on of not pulling the trigger early enough after he wormed his way into the area early in the second period, and Bridge's superb low cross seconds later was unfortunate not to find someone to tap it home.
Cheek flashed a shot harmlessly wide after reacting quickest to a blocked shot by sub, Sam Gregory and Gregory saw an even better opportunity on goal once again blocked moments later, with Soloman proving a difficult man to pass.
Despite the pressure, it wasn't until over half way through the second period before Timms was tested again and having thwarted Bridge early in the first half, Timms was at it again doing well to parry another first time effort from Bridge.
But having missed chance after chance after chance, there was almost an inevitability about Maidenhead's second coming with just over quarter of an hour left on the clock when Dave Tarpey doubled the home side's lead.
Having been at fault for the first goal, there was little Lovelock could do about this one saving Danny Green's initial effort with his feet, only to see Tarpey come in and beat Rob Girdlestone to the header to head into the unguarded net.
Chelmsford failed to stage any sort of a comeback as the sucker-punch of the second goal had knocked the wind out of the sails of the visitors, with the home side recording their first league win since Boxing Day.
1. Ashley Timms
2. De’Reece Vanderhyde
3. Leon Solomon
4. Ashley Nicholls (C)
5. Jacob Erskine
6. Simon Downer
7. Sam Barratt
8. Eddie Hutchinson
9. Tashan Adeyinka
10. Charlie Strutton
11. Dave Tarpey
12. Danny Green (On for Sam Barratt 58’)
14. Stefan Brown
15. Mark Nisbet (On for Simon Downer 16’)
16. Bobby Behzadi (On for Tashan Adeyinka 66’)
17. Sam Gray
1. Tom Lovelock
2. Rob Girdlestone
3. Michael Toner
4. Mark Hughes (C)
5. Harry Hickford
6. Yado Mambo
7. Lee Sawyer
8. Joe Ward
9. Jaanai Gordon
10. Michael Cheek
11. Jack Bridge
12. Leon Redwood
14. Sam Gregory (On for Jaanai Gordon 58’)
15. Rohdell Gordon (On for Rob Girdlestone 78’)
16. Harry Morgan
17. Kevin Maher
Referee: Wayne Porter (Bourne)
Assistants: Alistair Wilson (Boston) & Nathan Walker (King’s Lynn)
Maidenhead United: Tashan Adeyinka (10’), Dave Tarpey (74’)
Chelmsford City: None
Maidenhead United: None
Chelmsford City: None
City Man of the Match: Jack Bridge