Aussie Brendan Godfrey was the star man for the home side, securing match-winning figures of 6-29 in the Beckett League Premier.
Brian Heywood's patient 55 was the mainstay of Cayton's 116-9.
In reply, brothers Paul and Mark Harrison got Whitby off to a flying start, with Mark scoring 29 and skipper Paul seeing his team to victory with an unbeaten 60.
Staithes lost out by a narrow margin at Cloughton.
The visitors got off to a bright start, racing to 62-1 after just 10 overs, Ian Dixon leading the way with 48.
Simon Bowes added 29 but the introduction of spin changed the game in Cloughton's favour as Jake Dudding grabbed 6-48 and Stuart Harris 3-42 to skittle Staithes for 148.
Cloughton struggled in reply, sinking to 60-6 until Ben Luntley was joined at the crease by Damian Readman, the duo digging deep to steer Cloughton to a one-wicket win. Luntley hit a crucial 41 while Readman remained unbeaten on 32 to earn the points for Cloughton.
Lee Oliver was the pick of the Staithes attack with 5-53.
In Division B, Fylingdales were unpicked by Charlie Gray in their seven-wicket defeat at Wold Newton.
Gray claimed 5-45 as the visitors slumped to 126 all out, and then proceeded to smack an unbeaten 52 to earn the win.
Duncan Steele and Steve Crowther starred in Whitby 2nds' 120-run win at Nawton Grange 2nds in Division C.
Steele struck an unbeaten 84 in Whitby's 207-5, Andrew Marshall adding 43 and Rikki Lawrence scoring 32.
Crowther then claimed 6-24 as Grange slipped to 87 all out.
Ravenscar cruised to an 84-run success at home to Cloughton 2nds.
Jish Rewcroft led the way for the hosts with 66, while William Warwick hit 33 and Ivan Kirk 31.
Liam Salt, 34, and Michael Readman, 33, tried their best to get Cloughton back into the game but they sank to 116 all out.