Dave Challinor suffered his first defeat as Pools boss as Woking came from behind to claim three points at Kingfield Stadium on Saturday.
When Gime Toure stroked home a penalty midway through the first half, Pools looked in control and on course for another way win but the hosts stuck to their task and found a route back in to the game after the break.
Challinor opted to name an unchanged starting eleven for the trip to Surrey, though new loan signing Tyler Hamilton was included on the bench after joining from Hull City on Friday.
After a scrappy start to the game it was Pools who began to get on the front foot and Gus Mafuta had the first effort on goal only to see his shot deflected wide.
At the other end Max Kretzshmar tried his luck with a curling effort from twenty yards but it never looked like troubling Ben Killip and it flew well off-target.
Pools strung together a good move to open up some space for Josh Hawkes on the edge of the area but the midfield man dragged his shot past the post.
The key moment arrived midway through the first half when Hawkes played a lovely ball in behind the Woking defence for Luke James and he got goal side of the defender before being brought down in the area. The referee pointed to the spot and Toure did the rest with a confident penalty.
There was a chance for Nicky Featherstone to try and recreate his spectacular strike at Exeter when Mafuta’s drive was blocked in to his path twenty-five yards out but this time the midfielder sliced across his effort and it flew well wide.
Hawkes stung the gloves of Woking keeper Craig Ross three minutes before the break after he sharply turned inside from the left to hit a low drive on goal.
The Cards thought they had levelled things up in first half injury time when Josh Casey’s free-kick was nodded in by Kane Ferdinand but the celebrations were cut short by an offside flag and Pools took their lead in to the break.
Challinor’s side began the second half on the front foot and could have doubled their lead when Ryan Donaldson found space to shoot but his effort was charged down.
Pools continued to press and Mark Kitching got forward well on the left to let fly with two efforts in quick succession which were both blocked by some determined defending.
Woking then began to build some momentum of their own and they were level on 65 minutes when a long throw from the right was only half-cleared and the hosts kept it alive inside the box for top scorer Jake Hyde to sweep home from six yards.
Home substitute Paul Hodges was having a real impact and he tested Killip with a drive from the edge of the area which the Pools keeper held comfortably.
However, Killip was powerless to stop a wonderful shot from Dave Tarpey 12 minutes from time – the Woking front man drove inside from the right before despatching a brilliant curling effort in to the top corner.
Challinor threw Hamilton on for his debut and also introduced Nicke Kabamba in search of an equaliser but the home side managed the closing stages well for the most part.
Kenton Richardson came agonisingly close to nicking a point for Pools with the final act of the game when he met a left-wing corner with his head but it crashed back off the cross bar as the full-time whistle sounded.
Full Time: Woking 2 Pools 1
Woking: Ross, Cook, Casey, Collier, Gerring, Donnellan (Hodges 65), Ferdinand, Poku, Kretzschmar, Tarpey (Gray 87), Hyde.
Subs not used: Paulat-Brigg, Parry, Meite.
Booked: Cook, Poku, Casey.
Pools: Killip, Richardson, Raynes, Kerr, Kitching, Mafuta (Hamilton 81), Featherstone, Hawkes (Kabamba 86), Donaldson, James, Toure.
Subs not used: Crichlow-Noble, Kennedy, Muir.
Booked: Mafuta, Hawkes.
Attendance: 2,127 (205 Poolies).