Jonathan Gray defeated Lloyd Glasspool 6-3 6-2 in the M25 Norman 1 round of 32 on hard. The upset overturned the form book — Lloyd Glasspool came in leading the head-to-head 2–0. Jonathan Gray claimed a first win over Lloyd Glasspool in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-02-12 | Great Britain F3 | R32 | hard | Lloyd Glasspool | 7-6(6) 6-1 |
| 2017-09-18 | Great Britain F5 | R16 | hard | Lloyd Glasspool | 2-6 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.