Upon his return in 1999, Simmonds entered the 2000 World Championship, losing in the fifth pre-qualifying round. During the 2000/2001 season, he played on the Challenge Tour, reaching the semi-finals at Event 1 - where he lost 1–5 to Andrew Norman - and the quarter-finals at Event 3, where Kurt Maflin beat him 5–3, before reaching his first career final at Event 4. Drawn against nineteen-year-old Shaun Murphy, Simmonds lost 2–6, but his performances over the course of the season were sufficient for him to earn a place on the main tour.