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| WAFFL Charity Shield First Leg (Tuesday October 28th, 2008) |
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| Sabiya Wanderers | v | Dimi's Crusaders | 2-1 | Details |
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| WAFFL Charity Shield Second Leg (Tuesday January 27th, 2009) |
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| Dimi's Crusaders | v | Sabiya Wanderers | 3-1 | Details |
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| WAFFL Cup Round 1 (Saturday September 20th, 2008) |
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| 8th of May | v | Coco_Kickers | 5-4 | Details |
| Alma Rovers | v | Be Champions | 0-1 | Details |
| Bneid Al-Seaside | v | Spanish Villains | 5-2 | Details |
| Dimi's Crusaders | v | Mesolithic Albion | 0-1 | Details |
| Igrox Athletic | v | Scruffy's BarBarians | 5-0 | Details |
| Les Chats Noire | v | Kuwait Hearts | 1-0 | Details |
| Manilla Magic | v | The Chairmen | 2-4 | Details |
| North Seabreezers | v | The A-Team | 2-5 | Details |
| Philbert & Wanderus | v | Connecticut Huskies | 1-0 | Details |
| Real Salwagoza | v | Jone Salat Bangkok | 1-0 | Details |
| Road to Nowhere | v | Savo Corner 07 | 4-0 | Details |
| The Firm F.C. | v | Cloughies Red Nose | 3-0 | Details |
| The International Team Salwa | v | The Greasy Chip Buttie | 9-0 | Details |
| Thunder Bluff Boyz | v | The Auckland | 9-0 | Details |
| Weddell's Wanderers | v | Kirton Kickers | 2-0 | Details |
| What's Going On? | v | Neolithic Wanderers FC | 1-2 | Details |
| |
| WAFFL Cup Round 2 (Saturday November 8th, 2008) |
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| Athletico Squirros | v | Thunder Bluff Boyz | 1-0 | Details |
| Avondale Athletic | v | Varns Vagges | 0-2 | Details |
| Be Champions | v | Ibrox Reserves | 0-3 | Details |
| Bneid Al-Seaside | v | Weddell's Wanderers | 3-0 | Details |
| Fircombe Hall | v | The A-Team | 3-0 | Details |
| Nottm Orchard | v | Real Salwagoza | 2-0 | Details |
| Philbert & Wanderus | v | Mesolithic Albion | 1-0 | Details |
| Riyadh Surfer | v | Why Do Fools? | 1-0 | Details |
| Road to Nowhere | v | Neolithic Wanderers FC | 1-1 | Details |
| Sabiya Wanderers | v | Igrox Athletic Reserves | 0-3 | Details |
| Salwa Knackeredemicals | v | The Chairmen | 3-0 | Details |
| The Bastard Sons of Peter Beardsley | v | Ethynol Rangers | 0-1 | Details |
| The Firm F.C. | v | Degsie's Demons | 3-0 | Details |
| The International Team Salwa | v | Les Chats Noire | 0-2 | Details |
| Titi Floats On | v | Igrox Athletic | 1-0 | Details |
| Wilde Rovers | v | 8th of May | 1-0 | Details |
| |
| WAFFL Cup Round 2 Replays (Saturday November 15th, 2008) |
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| Neolithic Wanderers FC | v | Road to Nowhere | 0-2 | Details |
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| WAFFL Cup Round 3 (Saturday December 20th, 2008) |
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| Athletico Squirros | v | Ibrox Reserves | 5-0 | Details |
| Ethynol Rangers | v | Fircombe Hall | 0-1 | Details |
| Igrox Athletic Reserves | v | Varns Vagges | 4-0 | Details |
| Nottm Orchard | v | Riyadh Surfer | 0-1 | Details |
| Road to Nowhere | v | Les Chats Noire | 2-1 | Details |
| The Firm F.C. | v | Salwa Knackeredemicals | 1-1 | Details |
| Titi Floats On | v | Bneid Al-Seaside | 6-0 | Details |
| Wilde Rovers | v | Philbert & Wanderus | 1-0 | Details |
| |
| WAFFL Cup Round 3 Replays (Friday December 26th, 2008) |
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| Salwa Knackeredemicals | v | The Firm F.C. | 7-2 | Details |
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| WAFFL Cup Round 4 (Saturday February 7th, 2009) |
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| Athletico Squirros | v | Titi Floats On | 3-5 | Details |
| Riyadh Surfer | v | Fircombe Hall | 2-1 | Details |
| Road to Nowhere | v | Igrox Athletic Reserves | 3-3 | Details |
| Wilde Rovers | v | Salwa Knackeredemicals | 2-0 | Details |
| |
| WAFFL Cup Round 4 Replays (Saturday February 21st, 2009) |
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| Igrox Athletic Reserves | v | Road to Nowhere | 4-0 | Details |
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| WAFFL Cup Semi-Finals (Saturday March 21st, 2009) |
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| Riyadh Surfer | v | Titi Floats On | 0-1 | Details |
| Wilde Rovers | v | Igrox Athletic Reserves | 0-2 | Details |
| |
| WAFFL Cup Final (Saturday May 16th, 2009) |
|---|
| Titi Floats On | v | Igrox Athletic Reserves | 0-4 | Details |
