The Seadogs went to National League Harrogate Town, who were relegated from the Football League, just four months ago.
Boro came close on 27 minutes when Jack Waldron set up Mo Fadera who was denied by the Harrogate keeper.
Fadera's fellow former Woking player, Luke Hall put the visitors in front, moments later, sliding home a neat driven cross.
Fadera then fired into the side netting late in the first half.
Town levelled moments into the second half, before Dom Tear came close at the other end.
The hosts stepped it up, forcing Ryan Whitley into an excellent double save before Town won it, 2-1, with a late header.


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