| 19 May 2019 | First Round | Three Bridges v Old Wimbledonians | Three Bridges Road, Three Bridges | Results |
| 26 May 2019 | First Round | Alexandra Park v Hornsey | The Racecourse Ground, Alexandra Park | Results |
| 26 May 2019 | First Round | Banstead v Upminster | Recreation Ground, Banstead | Results |
| 26 May 2019 | First Round | Bishop's Stortford v Old Actonians | Cricketfield Lane, Bishop's Stortford | Results |
| 26 May 2019 | First Round | Broxbourne v Southall Dragons | Broxbourne Sports Club Ground, Broxbourne | Results |
| 26 May 2019 | First Round | Cockfosters v Shenfield | Chalk Lane, Cockfosters | Results |
| 26 May 2019 | First Round | Old Hamptonians v Wimbledon | Dean Road, Hampton | Results |
| 26 May 2019 | First Round | Stirlands v Chertsey | The Pavilion, Birdham | Results |
| 16 Jun 2019 | Second Round | Bexley v Upminster | Manor Way, Bexley | Results |
| 16 Jun 2019 | Second Round | Bickley Park v Blackheath | Bickley Park Road, Bickley | Results |
| 16 Jun 2019 | Second Round | Cambridge v Finchley | Clare College Sports Ground, Cambridge | Results |
| 16 Jun 2019 | Second Round | Chingford v Fives and Heronians | Forest Side, Chingford | Results |
| 16 Jun 2019 | Second Round | Hornchurch v Paragon | Harrow Lodge Park, Hornchurch | Results |
| 16 Jun 2019 | Second Round | Broxbourne v Aston Rowant | Broxbourne Sports Club Ground, Broxbourne | Results |
| 16 Jun 2019 | Second Round | Wimbledon v Bromley | Church Road, Wimbledon | Results |
| 16 Jun 2019 | Second Round | Shenfield v Hoddesdon | Old County Ground, Brentwood | Results |
| 16 Jun 2019 | Second Round | Three Bridges v Chertsey | Three Bridges Road, Three Bridges | Results |
| 16 Jun 2019 | Second Round | Old Actonians v Crouch End | Old Actonians Sport Club Ground, Ealing | Results |
| 16 Jun 2019 | Second Round | Oxted and Limpsfield v Reigate Priory | Master Park, Oxted | Results |
| 16 Jun 2019 | Second Round | Sandwich Town v Indian Gymkhana | The Butts, Sandwich | Results |
| 16 Jun 2019 | Second Round | Stanmore v Brentwood | Stanmore Common, Stanmore | Results |
| 16 Jun 2019 | Second Round | Sunbury v East Molesey | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 16 Jun 2019 | Second Round | Waltham v Hornsey | The Peter May Sports Centre, Walthamstow | Results |
| 16 Jun 2019 | Second Round | Wanstead and Snaresbrook v Acton | Overton Drive, Wanstead | Results |
| 07 Jul 2019 | Third Round | Chingford v Crouch End | Forest Side, Chingford | Results |
| 07 Jul 2019 | Third Round | Bexley v Shenfield | Manor Way, Bexley | Results |
| 07 Jul 2019 | Third Round | Blackheath v Acton | The Rectory Field, Blackheath | Results |
| 30 Jun 2019 | Third Round | Broxbourne v Sandwich Town | Broxbourne Sports Club Ground, Broxbourne | Results |
| 07 Jul 2019 | Third Round | Chertsey v East Molesey | Grove Road, Chertsey | Results |
| 04 Aug 2019 | Third Round | Cambridge v Reigate Priory | Clare College Sports Ground, Cambridge | Results |
| 07 Jul 2019 | Third Round | Hornchurch v Waltham | Harrow Lodge Park, Hornchurch | Results |
| 11 Aug 2019 | Third Round | Stanmore v Wimbledon | Stanmore Common, Stanmore | Results |
| 04 Aug 2019 | Quarter-Final | Crouch End v Bexley | The Calthorpe Ground, Crouch End | Results |
| 28 Jul 2019 | Quarter-Final | Acton v Hornchurch | Manor Park Grounds, Acton | Results |
| 18 Aug 2019 | Quarter-Final | East Molesey v Sandwich Town | Memorial Cricket Ground, East Molesey | Results |
| 25 Aug 2019 | Quarter-Final | Cambridge v Stanmore | Clare College Sports Ground, Cambridge | Results |
| 18 Aug 2019 | Semi-Final | Acton v Bexley | Manor Park Grounds, Acton | Results |
| 01 Sep 2019 | Semi-Final | Cambridge v East Molesey | Clare College Sports Ground, Cambridge | Results |
| 15 Sep 2019 | Final | Bexley v Cambridge | The Rectory Field, Blackheath | Results |
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