The Blues made it three years of successive wins over neighbours Guisborough Town as they retained the Micky Skinner Memorial Trophy on Tuesday night.
Darren Williams’ men, led by assistants Dave Campbell and Dennis Wheeler with Williams on holiday, had to come from behind however after a familiar face struck early on.
There was just 32 seconds on the clock when Nathan Mulligan put Guisborough ahead after a neat move.
The Blues had three debutants in their starting line-up- former Fleetwood and Carlisle youth forward Greg Peel, midfielder Stuart Bath, fresh from playing in the United States, and left-sided ex-Harrogate midfielder Liam Shepherd.
Former Nottingham Forest winger Ross Gardner and 22-year-old local lad Matty Brown returned after absences of two years or more.
Mulligan came close again after finding space on the left edge of the box but his lob over the onrushing Shane Bland, dropped narrowly wide.
Bland then denied Mulligan with a brave near-post block low to his left.
The Northern League First Division outfit had the better of the first half, but defenders Ibby Hassan and Richard Pell both came close.
The usual raft of changes followed after the break. Ged Dalton was another back in Whitby colours after spells at Pickering and Bridlington, with former Middlesbrough junior Matthew Waters, ex-West Auckland midfielder Stuart Banks and winger Anthony Callaghan, who had a spell early in his career at Sunderland, joined by local player Ryan Braithwaite (22), who was given a run at right-back.
The Blues noticably stepped it up a gear in the second half, with the introduction of Steven Snaith alongside Waters, giving added attacking impetus.
After the lively Callaghan fired just over from the edge of the area, it was Snaith who brought the Blues level, on 69 minutes. Racing clear, the 20-year-old slid the ball between keeper Danny Dixon and defender Scott Oldfield from the edge of the area.
With ten minutes remaining, the speedy Dalton then ran down the same flank, before cutting into the box and drawing a rash slide from Oldfield.
The penalty was despatched clinically by Craig Farrell, as Dixon fell the wrong way. Whitby Town: Bland, Hassan, Robinson (c), Burgess, Pell, Shepherd, Gardner, Bath, Farrell, Peel, Brown. Subs: Callaghan, Dalton, Snaith, Banks, Braithwaite, Waters, Bullock.