Pools are still looking for their first National League victory after losing out 2-1 at Maidenhead.
A goal in either half gave the hosts a strong advantage and, while Padraig Amond gave his side a glimpse of hope with a late penalty, Pools couldn't build on this as the game finished 2-1.
Liam Donnelly was called into action early on as he put in a strong challenge to deny harry Pritchard who was pushing into the box from the left.
Pritchard did make it into the box with the hosts next attack, getting on the end of a cross by the busy Dave Tarpey to send a header over the bar on four minutes.
Pools showed their first attacking threat just before ten minutes; Jake Cassidy was powerful on the half-way line and he got the ball up to Padraig Amond who tried to find Blair Adams at the far side with his cross, but the defender intercepted.
Another cross by Tarpey at the other end was bound for Ryan Upward until Carl Magnay got a block in to prevent the danger as the hosts looked to put pressure on Pools.
There was another flash for Pools as Lewis Hawkins picked out Liam Donnelly with a great diagonal ball. Donnelly showed a brilliant first touch to take it past his man but sent his shot high over the bar under pressure from a defender.
But as was the way for spells of the first half, the hosts were soon back on the attack and this time it was Sean Marks who got up to send a header over the bar.
A lucky bounce allowed Cassidy to get a cross in from the right but his ball bounced across the box untouched as there was no Pools man there to get a touch.
Blair Adams took the bull by the horns on the half hour mark to power into the box; he pushed his way deep into the box but just as he prepared to shoot, the ball was taken by a home shirt.
On 35 minutes Maidenhead took the lead and Pools once again found themselves behind in a game. It was real route one play from the hosts as keeper Carl Pentney sent the ball high up field where Marks flicked it on and Tarpey picked it up to roll past Loach and into the bottom corner.
Loach made a great save to deny Maidenhead a second just after; a corner was sent back at goal through a crowded box and the Pools keeper showed great reactions to get down to his right and palm away.
Pools had their best chance of the half late on as Ryan Donaldson pushed himself forward to play in Blair Adams, who was the brightest in this first half for Harrison’s side. Adams got the ball into the box for Cassidy who turned to shoot but could only find Pentney with his effort.
Harrison switched things round at half time, introducing Michael Woods to the action and changing from 3-5-2 to 4-4-2.
And Pools did look brighter, going close early on to getting the equaliser as a corner to the far post was headed back in by Amond, flicked back by Harrison and then fired goalwards by Cassidy just failed to force it home.
But just as Pools looked to be finding their way back into this game and once again showing an improved second-half display, Maidenhead doubled their lead.
Louis Laing slipped up in a dangerous position, kicking the ball straight into the path of the lively Tarpey and he didn’t need a second invitation as he ran in on goal and smashed the ball high into the net to make it 2-0.
With twenty minutes left, Scott Loach pulled off another top save, getting down well to his right again to block a shot from Tarpey, denying the striker his hat-trick.
As Pools looked for a lifeline, Adams sent a pacy cross in from the left which found only the arms of Pentney, while Scott Harrison met a Magnay freekick but sent his header just wide of the post.
Harrison had another shot on goal, this time poking the ball at goal following a corner but his effort was blocked out by Pentney.
Pools were seeing most of the ball by this stage and threw numbers forward but they just couldn’t find the net; Devante Rodney set up Amond to the left of the area but his low strike bobbled wide of the far post.
Devante Rodney showed strength to force his way past the defender and into the box from the right. The striker powered in and played in Carl Magnay who was bundled over as he fired a shot in at goal.
The referee awarded the penalty, which Padraig Amond stepped up to slot home to make it 2-1 with just four minutes left.
This set up for a lively finale to the game, with Deverdics seeing an effort blocked and Harrison having another saved, while Cassidy flicked on a Deverdics freekick but the ball fizzed out at the far post.
Scott Loach spared his side's blushes further with another great save late in the game, once again to deny Tarpey from firing home.
And so the game finished in defeat for Craig Harrison's side who go into Tuesday night's match with Chester at The Vic looking for their first win of the new season.
Full Time: Maidenhead United 2 Pools 1
Attendance: 1491 (259 Pools)
Booked: Newton (71)
Maidenhead United: Pentney, Clerima, Odametey, Massey, Tarpey, Comley, Marks (Clifton 65), Pritchard (Mulley 76), Upward (Inman 90), Kilman, Goodman.
Subs Not Used: Hyde, Barratt.
Pools: Loach, Magnay, Laing, Harrison, Donnelly (Deverdics 68), Donaldson (Rodney 68), Newton, Hawkins (Woods 46), Adams, Amond, Cassidy.
Subs Not Used: Featherstone, Munns.