Royston Gough's late header at Bridge on Saturday sent Canterbury into the Les Leckie Cup final.
With 10 minutes remaining, Scott Lawford sent over a corner to the near post where Gough outjumped the Oakwood defence to seal victory.
Canterbury boss Dave Fairclough said of Oakwood: “They gave us a tough game to draw at Bridge a fortnight ago and they came back almost as strongly in the cup.
“But our organisation has improved and it’s great to get another chance of putting some silverware on the table. But I’m glad we’re not facing Oakwood again this season.”
Oakwood proved a well-drilled side who relied on the exceptional goalkeeping of Clark Hunt to get them out of trouble.
Calum McGeehan, whose long passing repeatedly asked questions of the Oakwood defence, created the opening goal in the 13th minute. His shot was blocked by Hunt and the ball flew up for Lawford to head home.
The Maidstone side responded by closing ranks and City were unable to break through again in the first half.
Three minutes into the second half, Gough broke clear and sent in a shot that looked a goal all the way until Hunt clawed the ball away.
The outcome hung in the balance until the 80th minute when Gough had the final word.