Sherwood Stewart has a competitive grass court record of 35–40 across 75 matches (46.7%). The record shows a player capable of competing here, though there is clear room to push the win rate higher. Claimed 1 title on grass: Manchester.

At Grand Slam level (Wimbledon): Sherwood Stewart has struggled at Grand Slam level on grass: 9–17 (34.6%) in 26 matches. The best-of-five format and elite fields make this the toughest benchmark on this surface.

One final reached on grass, converted into a title — a perfect finals record on this surface. 2 semifinals. 5 quarterfinals.

vs. Top 10 on grass: 2–6 (25.0%, 8 matches). Top 10 opponents have represented a clear ceiling on grass; addressing that deficit is the single biggest lever for improving the overall record here.

By format on grass — best-of-five: 9–18 (33.3%); best-of-three: 26–22 (54.2%). Markedly stronger in three-set formats; the win rate drops noticeably in five-setters, which has direct implications for Grand Slam performance on grass.

Best season: 1973 — 7–4 (63.6%) from 11 matches. The best single-season display to date — a useful reference point as the grass record continues to develop.