Having missed out on one of the five available cards at Q School via a playoff in 2017, Shacklady returned in 2018 and earned his place on to the Legends Tour for the 2018 season. David followed that up with a debut victory at the Russian Open Golf Championship (Senior), finishing two strokes ahead of Stephen Dodd and Phillip Price. He also tied for third place in two events and finished 11th in the Order of Merit.
 
Shacklady continued his good form in the 2019 season where he tied for third place in two further events in the early part of the season before winning the Sinclair Invitational and the Paris Legends Championship in September.