Named for Kevin Ashman, the Ashman Trophy is awarded to the player with the highest average of correct 2 point answers during the league season who has played in at least half of their team's matches. With 6.25 out of 8 in the 2008-2009 season, the first winner was Kevin Ashman himself. Regular updates to the averages can be found in the Numbers section.
| Season | Winner | Team | Points |
| 2008-2009 | Kevin Ashman | Allsorts | 6.25 |
| Pos | Division 1 | P | W | D | L | Avg | B | Pts |
| 1 | Broken Hearts (C) | 20 | 17 | 1 | 2 | 52.90 | 14 | 84 |
| 2 | Pericardium | 20 | 16 | 2 | 2 | 50.95 | 9 | 77 |
| 3 | Nomads | 20 | 14 | 2 | 4 | 50.15 | 12 | 72 |
| 4 | Atletico | 20 | 13 | 1 | 6 | 47.85 | 8 | 62 |
| 5 | Allsorts | 20 | 12 | 1 | 7 | 47.35 | 4 | 54 |
| 6 | Old Itonians | 20 | 10 | 2 | 8 | 45.55 | 9 | 53 |
| 7 | Telstars | 20 | 8 | 0 | 12 | 42.00 | 5 | 37 |
| 8 | Barb | 20 | 5 | 1 | 14 | 38.70 | 5 | 27 |
| 9 | Pineapple | 20 | 4 | 1 | 15 | 37.65 | 4 | 22 |
| 10 | Waterloo Sunset | 20 | 3 | 0 | 17 | 37.40 | 1 | 13 |
| 11 | Five Bells | 20 | 2 | 1 | 17 | 38.10 | 1 | 11 |
| Pos | Division 2 | P | W | D | L | Avg | B | Pts |
| 1 | Gray Monks (W) | 20 | 17 | 0 | 3 | 48.75 | 9 | 77 |
| 2 | Banana Splits | 20 | 15 | 2 | 3 | 43.65 | 3 | 67 |
| 3 | Rosslyn Park | 20 | 13 | 0 | 7 | 39.85 | 5 | 57 |
| 4 | Eclectics | 20 | 12 | 1 | 7 | 40.80 | 4 | 54 |
| 5 | Accies | 20 | 12 | 0 | 8 | 38.25 | 3 | 51 |
| 6 | Sons of the Dessert | 20 | 10 | 1 | 9 | 39.40 | 6 | 48 |
| 7 | Mealy Bugs | 20 | 9 | 0 | 11 | 39.10 | 4 | 40 |
| 8 | Ovalytes | 20 | 8 | 1 | 11 | 38.20 | 4 | 38 |
| 9 | Outcasts | 20 | 5 | 1 | 14 | 34.05 | 7 | 29 |
| 10 | Wharfside | 20 | 2 | 2 | 16 | 29.70 | 2 | 14 |
| 11 | London Scottish | 20 | 3 | 0 | 17 | 29.90 | 1 | 13 |
| Pos | Table | P | W | D | L | 2s | Pts |
| 1 | Sussex | 9 | 7 | 0 | 2 | 100 | 14 |
| 2 | Oxford | 9 | 5 | 1 | 3 | 74 | 11 |
| 3 | Mastermind Club | 9 | 4 | 1 | 4 | 111 | 9 |
| 4 | London | 9 | 4 | 0 | 5 | 95 | 8 |
| 5 | Beds & Herts | 9 | 4 | 0 | 5 | 85 | 8 |
| 6 | Cambridge | 9 | 2 | 0 | 7 | 78 | 4 |