Craig Harrison's side conceded two late goals as Macclesfield Town came from behind to take the win at Victoria Park
A first-half Michael Woods goal had given Pools a deserved lead but, after dominating much of the game, things were undone with just five minutes remaining as the visitors first equalised and then grabbed a last-minute winner.
There was an early warning for Pools in the first minute as Keith Lowe got into the box to fire a shot in from close range, which went just wide of the post.
Pools grew into the game though and were soon on top; persistence from Jack Munns opened things up down the left to set Michael Woods running at goal but his final cross into the box just failed to find a blue shirt.
Conor Newton, who was busy for Pools in the first half, charged down the defender to steal possession and send a cross into the box. The ball was deflected out as far as Rhys Oates but his snap-shot went wide of target.
As Pools continued to press, there was neat play down the right between Munns, Woods and Newton, with a good turn and shot by the latter being saved by Shwan Jalal at the near post.
Woods lifted a ball over the top for Jake Cassidy who fired in a shot from outside the area that went over the bar, before Oates did well to win his side a corner, forcing a touch off the defender after a good ball upfield by Scott Harrison.
The visitors enjoyed a brief spell of pressure mid-way through the half and there was a decent chance for Scott Burgess who saw his shot from distance go just wide of Loach’s far post.
With Pools back on the attack, Newton had a shot blocked inside the area, while Cassidy watched a glancing header go wide of the post.
The breakthrough finally came for Harrison’s side on 38 minutes and it was more good work from Cassidy who pushed down the right to play it in for Woods. And the midfielder took a touch, picked his spot and sent the ball past Jalal to make it 1-0.
There was a real burst of action following the goal, with a good save from Loach at one end to deny Burgess, while at the other end Cassidy was denied by Jalal.
Pools, who took a deserved lead into the second half, came out after the break looking full of confidence and determination and there were early half chances for Cassidy, Woods and Newton.
Cal Magnay chipped an effort towards goal after another push upfield by Pools but the skipper, back in the side after six-game absence through injury, saw his effort go wide of the far post.
Conor Newton, who was impressive for Pools this afternoon, fired in a shot from distance which was kept out by Jalal as the hosts looked to add to their advantage.
As Pools continued to dominate, there were efforts from Munns, which went wide, and Oates, that was held by Jalal.
There was still work to do at the other end as Newton puts in a great block to deflect a shot out for a corner kick but the visitors were level on 85 minutes; a good cross in from sub Elliott Durrell on the right picked out Ryan Lloyd in the box and he made no mistake with a low finish past Loach.
It was a real blow for Pools who had dominate the large majority of possession this afternoon and had created enough chances to be further ahead in the game.
There were chances at both ends in the closing minutes but it was Macclesfield Town who unbelievably snatched the winning goal.
A header from Lloyd bounced back off the crossbar but Keith Lowe was allowed the freedom to meet the rebound and put the ball back past Loach to grab a late win for his team.
Full Time: Pools 1 Macclesfield Town 2
Attendance: 3082 (106 Macclesfield Town)
Booked: Magnay (82), Harrison (90)
Pools: Loach, Magnay, Harrison, Laing, Deverdics, Donnelly (Rodney 90), Woods (Hawkins 85), Newton, Munns (Adeloye 90), Cassidy, Oates.
Subs Not Used: Ledger, Adams.
Macclesfield Town: Jalal, Hodgkiss, Fitzpatrick, Lowe, Pilkington, Marsh (Kennedy 90), Lloyd, Hancox (Durrell 53), Whitehead, Burgess (Wilson 65), Whitaker.
Subs Not Used: Ramsbottom, Arthur.