The Blues take on Northern League First Division Boro Rangers at Middlesbrough FC on Monday.
The Championship side host the final of the North Riding Senior Cup with Town having knocked out Rangers' league rivals Northallerton Town and Guisborough Town to book their place at the Riverside Stadium.
Whitby last won the competition in 2017, when they beat Pickering Town, 3-1, at the same venue. They have lifted the trophy on six other occasions.
Scarborough Athletic are the defending champions but were knocked out by Guisborough in the quarter finals.
Town boss Nathan Haslam told club board member Paul Connolly, he's expecting Boro Rangers to come out fighting:
Haslam says while he and the players can't wait the final is a reward for the hard work of volunteers at the club and the backing from supporters:
Several of the Blues players have Teesside connections- youngsters Max Howells and Ben Beals are on loan from Boro- with several players, including goalkeeper Shane Bland, midfielder Joe Wheatley and strikers Stephen Walker and Brad Fewster- having represented the club previously.
Haslam admits it's a dream come true for some of the Middlesbrough supporters at the club too:
Kick-off at the Riverside Stadium is 7.30pm with penalties to follow if scores are level after 90 minutes.
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