Last-32 finishes at three ranking events followed in the 1988/1989 season. At the 1988 Canadian Masters, Roscoe lost 1–5 to David Taylor; the 1988 UK Championship ended with a 3–9 defeat to Stephen Hendry, the 1989 British Open a 3–5 loss to Tony Meo. Roscoe's 1989 World Championship campaign began and finished with a 9–10 first-round qualifying defeat to sixty-year-old Jack Fitzmaurice.