Welshman Eifion Williams broke Swansea hearts as his injury time equaliser snatched all three points away from Kenny Jackett's promotion hopefuls.
The Hartlepool hit-man struck two minutes into injury time to cancel out a first-half opener from Leon Britton.
Despite the draw, Swansea remain in third place.
Swansea City: Gueret, Ricketts, Tate, Monk, Iriekpen, Martinez, Britton, Robinson, McLeod, Akinfenwa (Forbes 85), Knight (Trundle 64).
Subs Not Used: Watt, Austin, Murphy.
Booked: Ricketts.
Hartlepool: Konstantopoulos, Barron, Nelson, Nash, Humphreys, Strachan (Bullock 88), Sweeney, Clark (Walker 81), Butler (Eifion Williams 27), Daly, Pittman.
Subs Not Used: Clarke, Darren Williams.
Booked: Konstantopoulos, Eifion Williams.
Att: 13,960
Ref: L Probert (Gloucestershire).
Swans boss Kenny Jackett made two changes to the team that drew 1-1 at Bradford last Saturday with Izzy Iriekpen returning from injury to replace Kevin Austin in the heart of the defence, while Kevin McLeod came in for Tom Williams who was ruled out with a groin strain.
There was also good news for Swans fans with Lee Trundle starting his comeback from an ankle injury with a place on the substitutes bench.
Trundle had been out since the goalless draw at Swindon on New Year's Eve.
It meant Adebayo Akinfenwa and Leon Knight continued up front with Knight hoping to add to his debut hat-trick against the MK Dons 11 days previous.
Fellow new signing Steven Watt also made his Liberty Stadium bow with a place on the bench following the central defender's move from Chelsea.
They faced a Hartlepool side sitting just above the relegation zone in 18th place.
The Pools included new signing Jon-Paul Pittman in attack following his loan move from Nottingham Forest, along with defender Gerard Nash who moved on a loan deal from Ipswich.
Former Barry Town striker Eifion Williams returned from injury to take his place on the bench.
The two sides battled out a 2-2 draw in the north east back in September courtesy of a Trundle double.
Swansea were slow to settle as the visitors enjoyed the opening five minutes before neat build up play saw Kevin McLoed's cross come off the top of the bar.
Pools' Antony Sweeney did have the ball in the back of the Swansea net in the eighth minute, but the whistle had already gone for offside.
But at least Hatlepool looked as if they had come to play an open game - a philosophy which has suited Swansea in the past.
They responded immediately when Sam Ricketts did well down the left to pick out Akinfenwa with a perfect cross, but the big hit man failed to get enough power on his header to beat Dimitrios Konstantanopoulos from eight yards.
As play swung to both ends, Thomas Butler cut inside Alan Tate and Roberto Martinez before testing Willy Gueret with a shot from the edge of the area which the Swansea 'keeper got down well to save with 13 minutes gone.
Swansea were starting to get their passing game together, however, as Akinfenwa just failed to connect properly with a McLeod cross which Konstantanopoulos saved.
But the breakthrough came in the 20th minute when Akinfenwa challenged Konstantanopoulos for a Tate cross. The Pools 'keeper failed to gather and as the ball dropped Leon Britton was perfectly placed to fire home from six yards for his third goal of the season.
The visitors had to reshuffle in the 26th minute when Thomas Butler pulled up with a hamstring injury, to be replaced by former Wales B international Eifion Williams.
Williams slotted into a midfield role as Jon Daly fired a looping shot just over Gueret's bar with 30 minutes on the clock.
Swansea had a great shout for a penalty just before the interval when Britton was brought down by Konstantanopoulos, but referee Lee Probert waved play on.
Half-time: Swansea City 1 Hartlepool 0
Hartlepool came out for the second-half fired up and enjoyed a good 10 minute spell before Swansea stepped up a gear as the large crowd got behind their team.
McLeod fired a shot wide after good battling by Knight who was finding it difficult to find the openings.
But just as the home side were starting to enjoy a better share of possession, they were nearly rocked back on their heals just before the hour mark when Pittman struck the bar with a fierce shot.
It gave Swansea a timely reminder that they still had a lot to do to win the game as Andy Robinson, who was having a good game in the middle of midfielder, fired a long range shot just over.
They were reminded again in the 62nd minute when Pittman won a free kick on the edge of the area. Gavin Strachan stepped up to take it and his curling effort looked to be heading for the top corner only for Gueret to pull off a great save.
It was enough for Jackett to send on Lee Trundle two minutes later as Knight made way for Swansea's top scorer.
Hartlepool were still searching for the equaliser though as they won a succession of corners which Swansea did well to defend.
Eventually Swansea came forward as McLeod fired a shot inches the wrong side of the far post.
But back the visitors came as Pittman won a free kick near the by-line with 72 minutes gone. Strachan whipped it in, but Williams' touch just went wide with Daly coming in at the far post.
Swansea kept giving the ball away in frustrating fashion before rallying for the final 15 minutes as a bit of Trundle magic nearly set up Akinfenwa.
With 10 minutes remaining, Hartlepool sent on James Walker for Ben Clark in a last attempt to snatch a point.
Swansea responded in the 85th minute as Adrian Forbes replaced Akinfenwa.
But just when Swansea looked to be heading for a vital win, they suffered a bitter low two minutes into injury time when the visitors grabbed the equaliser.
A long throw from Ritchie Humphries caused confusion in the Swansea box and after the home side failed to clear, Pittman managed to find Eifion Williams outside him and he broke the hearts of the home fans by firing beyond Gueret.
The only thing left for the referee to do was to blow the final whistle on a disappointing second half performance as Hartlepool deserved the share of the spoils.
