Former Pools player Gus Mafuta returned to The Vic for the first time since leaving in the summer and sealed the tie as Pools were defeated 2-1.
A shaky opening 15 minutes led to neither side creating any clear cut chances. Molyneux continuously looked a threat for Pools.
The first big chance of the game came on the half hour mark as a ball towards the back post looked certain to be put in by Holohan but his header was denied Ashmore who saved excellently.
Boreham Wood would then take their chance to attack just five minutes later as the ball broke for Tshimanga on the edge of the box and his effort was well saved by Ravas.
The first goal of the game came after 37 minutes, when the Boreham corner bounced around in the box and it was struck by former Pools man Gus Mafuta who made it 1-0 to The Wood.
Hartlepool continued to search for the equaliser before the half time whistle but Ashmore once again denied Pools and Luke Molyneux with another great save.
That Pools goal finally came right on the brink of half time. A ball into the box was scrambled of the goal line by Ashmore but Mason Bloomfield was at the right place at the right time to slot in his first league goal of the season.
Challinor's men started the second half with the dominance of possession and some patient build-up play led to a near chance. Some forward passing around the box then falls to Holohan who shoots narrowly wide against the side netting.
Pools were once again regretting those missed chances as after 66 minutes, it was that man again Gus Mafuta who picked up the ball around 25 yards out and fired in Boreham Wood's second after the defence failed to close him down.
Substitute Joe Grey tried to get Pools back into the game and his effort came close but was well defended and blocked by the Boreham Wood defence.
A disappointing night for Dave Challinor and his team will look to bounce back for Tuesday nights game against King's Lynn.
SUBS:
68: Ofosu on for Donaldson
69: Oates on for Crawford
78: Grey for Molyneux
Cards
Nicky Featherstone 67'