| 2 | February | | | | |
| FixtureId | FixtureYear | Date | Name | Time | Venue |
| 112 | 2019 |
Friday 1
| Annual Dinner |
18:45
| Olton Golf Club |
|
| 4 | April | | | | |
| FixtureId | FixtureYear | Date | Name | Time | Venue |
| 113 | 2019 |
Thursday 25
| President's Team v Captain's Team & AGM |
15:00
| Olton Golf Club |
| 114 | 2019 |
Sunday 28
| OSGS Team v The School |
13:30
| Olton Golf Club |
|
| 5 | May | | | | |
| FixtureId | FixtureYear | Date | Name | Time | Venue |
| 115 | 2019 |
Wednesday 8
| Wiseman Cup Greensomes |
15:00
| Olton Golf Club |
| 116 | 2019 |
Saturday 11
| Grafton Morrish Qualifying |
10:00
| Olton Golf Club |
| 117 | 2019 |
Thursday 16
| "B" Team v Avenue Bowling Club |
15:00
| Olton Golf Club |
| 118 | 2019 |
Wednesday 22
| "A" Team v Ladbrook Park Golf Club |
15:00
| Ladbrook Park Golf Club |
|
| 6 | June | | | | |
| FixtureId | FixtureYear | Date | Name | Time | Venue |
| 119 | 2019 |
Thursday 13
| "B" Team v Olton Golf Club |
14:30
| Olton Golf Club |
| 120 | 2019 |
Thursday 20
| OSA Challenge Cup (Open to any Old Silhillian or Staff) |
14:30
| Olton Golf Club |
|
| 7 | July | | | | |
| FixtureId | FixtureYear | Date | Name | Time | Venue |
| 121 | 2019 |
Wednesday 3
| "B" Team v Old Edwardians Golfing Society |
16:00
| Olton Golf Club |
| 122 | 2019 |
Thursday 11
| Invitation AM-AM (Roy Letts Memorial Salver) |
15:00
| Olton Golf Club |
| 123 | 2019 |
Tuesday 16
| "B" Team v Old Veseyans Golfing Society |
15:30
| Moor Hall Golf Club |
| 124 | 2019 |
Tuesday 23
| "A" Team v Robin Hood Golf Club |
15:00
| Olton Golf Club |
|
| 8 | August | | | | |
| FixtureId | FixtureYear | Date | Name | Time | Venue |
| 125 | 2019 |
Saturday 10
| "A" Team v Olton Golf Club (followed by lunch) |
08:30
| Olton Golf Club |
| 126 | 2019 |
Thursday 15
| "A" Team v Copt Heath Golf Club |
15:00
| Copt Heath Golf Club |
| 127 | 2019 |
Friday 30
| Captain's Away Day (Coach from OSA Clubhouse) |
07:45
| Broadway Golf Club |
|
| 10 | October | | | | |
| FixtureId | FixtureYear | Date | Name | Time | Venue |
| 128 | 2019 |
Thursday 3
| The Norfolking Cup |
10:30
| Heachem Manor Golf Club |
| 129 | 2019 |
Friday 4
| Grafton Morrish Finals |
00:00
| Hunstanton Golf Club |
| 130 | 2019 |
Sunday 6
| Le Strange Hotel Reserved for Solihull Party |
00:00
| & Royal West Norfolk Golf Club |
|
| 12 | December | | | | |
| FixtureId | FixtureYear | Date | Name | Time | Venue |
| 131 | 2019 |
Saturday 14
| OSA December Vase & Lunch (Shot Gun Start) |
08:00
| Olton Golf Club |
|