Maidenhead United came from a goal down to win 2-1 and consign Pools to a fifth successive defeat.
Craig Harrison's side had taken a first-half lead through Jake Cassidy but, after failing to capitalise further, were punished in the second half as the visitors struck twice to take the three points.
There was a lively start to the game, with early chances at both ends as Rhys Oates drilled one wide for Pools and Harold Odametey did the same with his effort for the visitors.
Jonathan Franks cut in from the right and fired a warning shot at goal on seven minutes that went wide of the near post as Pools looked to get off to the right start.
On ten minutes the action was back at the opposite end as Max Kilman crossed into the box for the dominant Sean Marks to head down into the path of Harry Pritchard. But with the goal in his sights, Pritchard took the option to get down and head the ball and found only the arms of Scott Loach.
Pritchard had another punt from long range shortly after but again it was easy for Loach.
Oates grew into the game for Pools and was a real threat down both wings, forcing the team forward and, on 25 minutes he had a great chance on goal. The Pools forward was picking out his spot with a decent effort onto to be denied by Rene Steer with a great block.
Kenton Richardson arrived to fire in a low drive through the crowd at goal but his effort was blocked wide and, according to the appeals from the Pools player, it hit a defender’s hand in the process but the referee awarded only the corner.
Less than five minutes later and Pools were ahead; Nicky Deverdics puts a great ball in from the right which picks out Jake Cassidy in the box and he gets up to meet the ball and send it past Carl Pentney to make it 1-0.
It was nearly 2-0 shortly after as Oates caused problems down the left, skipped past his man and crossed the ball in for Michael Woods running into the box. But just as it looked like Woods was set to double the lead, Steer popped up once more to block the shot.
Pools lost Kenton Richardson to injury after the right back was challenged when skipping upfield with the ball and Scott Harrison came on to replace him.
Deverdics sent a decent freekick into the box which found Rhys Oates in plenty of space but this time the header went over the bar as Pools looked for a crucial second goal.
Franks set up Cassidy for the final real chance of the half but the big striker sent his header just over the bar and Pools went in 1-0 up at the break.
Harrison’s side started the second half brightly and there were early chances for Pools as Conor Newton had an effort cleared off the line and Jonathan Franks caused problems from the left.
But it was the visitors who were next to find the back of the net, breaking forward to get the equaliser on 52 minutes through the busy Sean Marks.
The second half was a niggly affair, with some dubious challenges and plenty of yellow cards stopping either team from getting into their flow, and Pools looked for someone to add the much-needed spark.
Scott Loach made a great save to deny Harry Pritchard from close range just after the 70th minute as the visitors remained a threat on the break.
And then on 77 minutes, Maidenhead took the lead; Loach saved again from Pritchard but with no one in a home shirt reacting quick enough, Marks nipped in and sent the rebound back past the Pools keeper and into the back of the net to make it 2-1.
Pools had plenty of the ball in the remainder of the half but could not find enough to get another goal and the game finished in defeat.
Full Time: Pools 1 Maidenhead United 2
Attendance: 2756 (40 Maidenhead United)
Booked: Harrison (45), Laing (49), Newton (63)
Pools: Loach, Richardson (Harrison 40), Laing, Donnelly, Adams (Rodney 66), Newton, Woods, Deverdics, Franks, Cassidy (Simpson 82), Oates.
Subs Not Used: Catterick, Munns.
Maidenhead United: Pentney, Clerima, Steer (Mulley 70), Odametey, Massey, Emmanuel (Clifton 67), Marks (Hyde 81), Pritchard, Kilman, Goodman, Smith.
Subs Not Used: Owusu, Peters.