Whitby made 277-9 batting first against Stokesley but they could only manage a winning draw.
Theo Clarke led the Whitby charge with a superb 86, and he was ably supported by Aaron Leeman, 56, Paul Buck, 50, Jonathan Chapman, 29 not out, and Finlay Morris, 25, as they posted a very strong total.
Stokesley struggled with the bat, but frustrated Whitby to finish on 119-6 from 50 overs to deny their hosts the win.
Chapman led the way with the cherry, taking 3-32 for Whitby, while the other wickets came from James Hall, 2-29, and William Donald, 1-28.
Whitby 2nds were hammered on the road at Shildon Railway in Division Two of the North Yorkshire South Durham League.
Five of Whitby's batsmen failed to get off the mark as they were bundled out for just 62 in 29.4 overs.
Ian Suckling made 18 of those runs, while Jack Lyth made 11 before he was run out and Andrew Wood also made it to double figures.
The hosts found batting much easier as Whitby only managed one breakthrough as Joseph Husband removed opener Greg Upton for 31 before Shildon's Martin Worthington and Bret Upton knocked the runs off with ease.