Captain Joel Pope (44) and Thushara Managei (40) helped their side stumble to 182 all out as Adam Dyson 5-50 dominated proceedings at Hanger Hill.
But Epsom-born England U19 star Winslade and Sarel Erwee (3-27) proved equally as tricky to face as the hosts eased to victory.
Weybridge will hope to back that showing up when they make the short trip to winless Banstead tomorrow.
All rounder Will Sabey was his side's key contributor for a third successive week as Malden Wanderers beat Cheam by seven wickets in Division One.
The 28-year-old claimed 6-37 to help dismiss the visitors for 111 and then teamed up with Alan Cope (37) for a 41-run partnership that got their side over the line.
Esher’s hopes of securing promotion to the top flight suffered a blow as they fell 30 points adrift of the Division One top two.
Opening bowler Dan Taylor’s 5-38 was not enough as his side lost at second placed Beddington.
Taylor took his season’s haul to 15 wickets with his best return of a campaign that sees his side fourth in the table.
Esher were dismissed for 121 – thanks largely to Sohail Ahmed (33) and Jonathan Barrett (34) – and Beddington needed just 38.4 overs to reach their winning target.
Four wickets each for East Molesey pair Ross Paxton (4-47) and Gayan Sirisoma (4-91) dismissed hosts Cranleigh for 205 in Division One.
But captain Sam Burge’s side struggled in reply and subsided to 132 all out with Andrew Westphal (38) providing the best resistance.
Andrew Milnes (4-41) and Bainbridge combined to hold the hosts to 196-7 and Walton reached 192-9, with Shaun Cox chipping in with 41.
In Division Four, Kingstonian collapsed in the face an inspired spell of bowling as they lost by 83-runs at Guildford City.
Ks bowler Sufiyan Munir claimed 5-62 as the hosts were dismissed for 203, Guildford’s Sajith Dissanayaka bettered that with 6-18 as the visitors were dismissed for 120.
Fixtures: Banstead v Weybridge, East Molesey v Farnham, Esher v Camberley, Old Whitgiftians v Malden Wanderers, Walton v Epsom, Kingstonian v Old Emanuel.