| Alan R. Schumann O40 Men's Challenge Cup | ||||||
| Team | Group A | Group B | Group C | Group D | ||
| 1 | Cheshire Azzurri | Shelton Kickers | Guilford Black Eagles | Falcon Polonia | ||
| 2 | Club Napoli | Greenwich Gunners | FC New Britain United | Greenwich Arsenal | ||
| 3 | South East Xara | Waterbury Ponte | Connecticut Storm | Bridgeport United | ||
| 4 | HK Cougars | North Branford Masters | Cheshire Inter | Albanians United | ||
| Group Play | ||||||
Home Teams Listed First |
||||||
| 5/11/2008 | 1v2 | 3v4 | ||||
| 6/15/2008 | 2v3 | 4v1 | ||||
| 6/29/2008 | TBD | TBD | ||||
| Round One - 05/11/08 | ||||||
| Group A | ||||||
| Home | Score | Away | Score | |||
| Cheshire Azzurri | 4 | Club Napoli | 0 | |||
| South East Xara | 4 | HK Cougars | 1 | |||
| Group B | ||||||
| Home | Score | Away | Score | |||
| Shelton Kickers | 1 | Greenwich Gunners | 0 | |||
| Waterbury Ponte | 3 | North Branford Masters | 1 | |||
| Group C | ||||||
| Home | Score | Away | Score | |||
| Guilford Black Eagles | 9 | FC New Britain United | 2 | |||
| Connecticut Storm | 10 | Cheshire Inter | 0 | |||
| Group D | ||||||
| Home | Score | Away | Score | |||
| Falcon Polonia | 3 | Greenwich Arsenal | 0 | |||
| Bridgeport United | 0 | Albanians United | 2 | |||
| Round Two - 06/15/08 | ||||||
| Group A | ||||||
| Home | Score | Away | Score | |||
| Club Napoli | 0 | South East Xara | 8 | |||
| HK Cougars | 0 | Cheshire Azzurri | 6 | |||
| Group B | ||||||
| Home | Score | Away | Score | |||
| Greenwich Gunners | 7 | Waterbury Ponte | 0 | |||
| North Branford Masters | 1 | Shelton Kickers | 4 | |||
| Group C | ||||||
| Home | Score | Away | Score | |||
| FC New Britain United | 3 | Connecticut Storm | 4 | |||
| Cheshire Inter | 2 | Guilford Black Eagles | 5 | |||
| Group D | ||||||
| Home | Score | Away | Score | |||
| Greenwich Arsenal | 3 | Bridgeport United | 2 | |||
| Albanians United | 1 | Falcon Polonia | 1 | |||
| Round Three - 06/29/08 | ||||||
| Group A - * Tentative 1 game to be played | ||||||
| Home | Score | Away | Score | |||
| Club Napoli | 5 | HK Cougars | 3 | |||
| Cheshire Azzurri | 1 | South East Xara | 1 | |||
| Group B | ||||||
| Home | Score | Away | Score | |||
| Waterbury Ponte | 0 | Shelton Kickers | 5 | |||
| North Branford Masters | 0 | Greenwich Gunners | 7 | |||
| Group C | ||||||
| Home | Score | Away | Score | |||
| Guilford Black Eagles | 1 | Connecticut Storm | 0 | |||
| Cheshire Inter | 0 | FC New Britain United | 4 | |||
| Group D | ||||||
| Home | Score | Away | Score | |||
| Greenwich Arsenal | 0 | Albanians United | 1 | |||
| Bridgeport United | 0 | Falcon Polonia | 9 | |||
| Quarter Finals - 08/10/08 | ||||||
| Game 01 | ||||||
| Home | Score | Away | Score | |||
| South East Xara | 3 | Greenwich Gunners | 1 | |||
| Game 02 | ||||||
| Home | Score | Away | Score | |||
| Shelton Kickers | 2 | Cheshire Azzurri | 3 | |||
| Game 03 | ||||||
| Home | Score | Away | Score | |||
| Guilford Black Eagles | 5 | Albanians United | 1 | |||
| Game 04 | ||||||
| Home | Score | Away | Score | |||
| Falcon Polonia | 0 | Connecticut Storm | 3 | |||
| Semi Finals - Date, Time and Sites - TBD | ||||||
| Game 01 | ||||||
| Home | Score | Away | Score | |||
| South East Xara | Guilford Black Eagles | |||||
| Game 02 | ||||||
| Home | Score | Away | Score | |||
| Cheshire Azzurri | Connecticut Storm | |||||