| 31 May 1999 | | Walmley v Old Edwardians | The John Findlay Memorial Ground, Walmley | Results |
| 17 Jul 1999 | | Studley v Old Edwardians | Washford Fields, Studley | Results |
| 28 Aug 1999 | | Old Edwardians v Walmley | The Memorial Ground, Solihull | Results |
| 30 Aug 1999 | | Moseley Ashfield v Old Edwardians | Yardley Wood Road, Moseley | Results |
| 03 May 1999 | | Aldridge v Old Edwardians | The Green, Aldridge | Results |
| 22 May 1999 | | Old Edwardians v Redditch | The Memorial Ground, Solihull | Results |
| 19 Jun 1999 | | Old Edwardians v Pelsall | The Memorial Ground, Solihull | Results |
| 10 Jul 1999 | | Old Edwardians v Lichfield | The Memorial Ground, Solihull | Results |
| 31 Jul 1999 | | Kenilworth v Old Edwardians | Warwick Road, Kenilworth | Results |
| 04 Sep 1999 | | Old Edwardians v Penn | The Memorial Ground, Solihull | Results |
| 24 Jul 1999 | | Old Edwardians v Aldridge | The Memorial Ground, Solihull | Results |
| 18 Sep 1999 | | Old Edwardians v Bedworth | The Memorial Ground, Solihull | Results |
| 11 Sep 1999 | | Pelsall v Old Edwardians | Walsall Road, Pelsall | Results |
| 12 Jun 1999 | | Penn v Old Edwardians | Mount Road, Penn | Results |
| 03 Jul 1999 | | Worcester Norton Taverners v Old Edwardians | Brockhill Lane, Norton | Results |
| 17 Apr 1999 | | Old Edwardians v Worcester Norton Taverners | The Memorial Ground, Solihull | Results |
| 24 Apr 1999 | | Lichfield v Old Edwardians | Collins Hill, Lichfield | Results |
| 01 May 1999 | | Old Edwardians v Studley | The Memorial Ground, Solihull | Results |
| 08 May 1999 | | Old Edwardians v Kenilworth | The Memorial Ground, Solihull | Results |
| 15 May 1999 | | Water Orton v Old Edwardians | Coleshill Road, Water Orton | Results |
| 29 May 1999 | | Old Edwardians v Evesham | The Memorial Ground, Solihull | Results |
| 05 Jun 1999 | | Old Edwardians v Moseley Ashfield | The Memorial Ground, Solihull | Results |
| 26 Jun 1999 | | Bedworth v Old Edwardians | Miners Welfare Park, Bedworth | Results |
| 07 Aug 1999 | | Old Edwardians v Water Orton | The Memorial Ground, Solihull | Results |
| 14 Aug 1999 | | Redditch v Old Edwardians | Bromsgrove Road, Redditch | Results |
| 21 Aug 1999 | | Evesham v Old Edwardians | Evesham Sports Club Ground, Evesham | Results |
| 11 Sep 1999 | | Bedworth v Evesham | Miners Welfare Park, Bedworth | Results |
| 11 Sep 1999 | | Lichfield v Water Orton | Collins Hill, Lichfield | Results |
| 18 Sep 1999 | | Evesham v Worcester Norton Taverners | Evesham Sports Club Ground, Evesham | Results |
| 18 Sep 1999 | | Kenilworth v Aldridge | Warwick Road, Kenilworth | Results |
| 18 Sep 1999 | | Moseley Ashfield v Pelsall | Yardley Wood Road, Moseley | Results |
| 18 Sep 1999 | | Redditch v Lichfield | Bromsgrove Road, Redditch | Results |
| 18 Sep 1999 | | Walmley v Penn | The John Findlay Memorial Ground, Walmley | Results |
| 18 Sep 1999 | | Water Orton v Studley | Coleshill Road, Water Orton | Results |
| 24 Jul 1999 | | Bedworth v Walmley | Miners Welfare Park, Bedworth | Results |
| 24 Jul 1999 | | Evesham v Kenilworth | Evesham Sports Club Ground, Evesham | Results |
| 24 Jul 1999 | | Lichfield v Penn | Collins Hill, Lichfield | Results |
| 24 Jul 1999 | | Moseley Ashfield v Studley | Yardley Wood Road, Moseley | Results |
| 24 Jul 1999 | | Pelsall v Worcester Norton Taverners | Walsall Road, Pelsall | Results |
| 24 Jul 1999 | | Redditch v Water Orton | Bromsgrove Road, Redditch | Results |
| 04 Sep 1999 | | Aldridge v Studley | The Green, Aldridge | Results |
| 04 Sep 1999 | | Water Orton v Worcester Norton Taverners | Coleshill Road, Water Orton | Results |
| 10 Jul 1999 | | Evesham v Studley | Evesham Sports Club Ground, Evesham | Results |
| 10 Jul 1999 | | Moseley Ashfield v Worcester Norton Taverners | Yardley Wood Road, Moseley | Results |
| 10 Jul 1999 | | Pelsall v Walmley | Walsall Road, Pelsall | Results |
| 10 Jul 1999 | | Penn v Bedworth | Mount Road, Penn | Results |
| 10 Jul 1999 | | Redditch v Aldridge | Bromsgrove Road, Redditch | Results |
| 10 Jul 1999 | | Water Orton v Kenilworth | Coleshill Road, Water Orton | Results |
| 17 Jul 1999 | | Aldridge v Evesham | The Green, Aldridge | Results |
| 17 Jul 1999 | | Bedworth v Pelsall | Miners Welfare Park, Bedworth | Results |
| 17 Jul 1999 | | Kenilworth v Redditch | Warwick Road, Kenilworth | Results |
| 17 Jul 1999 | | Moseley Ashfield v Lichfield | Yardley Wood Road, Moseley | Results |
| 17 Jul 1999 | | Walmley v Water Orton | The John Findlay Memorial Ground, Walmley | Results |
| 17 Jul 1999 | | Worcester Norton Taverners v Penn | Brockhill Lane, Norton | Results |
| 17 Apr 1999 | | Walmley v Kenilworth | The John Findlay Memorial Ground, Walmley | Results |
| 01 May 1999 | | Redditch v Kenilworth | Bromsgrove Road, Redditch | Results |
| 03 May 1999 | | Kenilworth v Evesham | Warwick Road, Kenilworth | Results |
| 15 May 1999 | | Kenilworth v Moseley Ashfield | Warwick Road, Kenilworth | Results |
| 22 May 1999 | | Penn v Kenilworth | Mount Road, Penn | Results |
| 29 May 1999 | | Kenilworth v Pelsall | Warwick Road, Kenilworth | Results |
| 31 May 1999 | | Bedworth v Kenilworth | Miners Welfare Park, Bedworth | Results |
| 05 Jun 1999 | | Kenilworth v Worcester Norton Taverners | Warwick Road, Kenilworth | Results |
| 12 Jun 1999 | | Lichfield v Kenilworth | Collins Hill, Lichfield | Results |
| 19 Jun 1999 | | Kenilworth v Studley | Warwick Road, Kenilworth | Results |
| 26 Jun 1999 | | Aldridge v Kenilworth | The Green, Aldridge | Results |
| 03 Jul 1999 | | Kenilworth v Walmley | Warwick Road, Kenilworth | Results |
| 07 Aug 1999 | | Moseley Ashfield v Kenilworth | Yardley Wood Road, Moseley | Results |
| 14 Aug 1999 | | Kenilworth v Penn | Warwick Road, Kenilworth | Results |
| 21 Aug 1999 | | Pelsall v Kenilworth | Walsall Road, Pelsall | Results |
| 28 Aug 1999 | | Kenilworth v Bedworth | Warwick Road, Kenilworth | Results |
| 30 Aug 1999 | | Worcester Norton Taverners v Kenilworth | Brockhill Lane, Norton | Results |
| 04 Sep 1999 | | Kenilworth v Lichfield | Warwick Road, Kenilworth | Results |
| 11 Sep 1999 | | Studley v Kenilworth | Washford Fields, Studley | Results |
| 17 Apr 1999 | | Evesham v Lichfield | Evesham Sports Club Ground, Evesham | Results |
| 17 Apr 1999 | | Moseley Ashfield v Bedworth | Yardley Wood Road, Moseley | Results |
| 17 Apr 1999 | | Penn v Pelsall | Mount Road, Penn | Results |
| 17 Apr 1999 | | Redditch v Studley | Bromsgrove Road, Redditch | Results |
| 17 Apr 1999 | | Water Orton v Aldridge | Coleshill Road, Water Orton | Results |
| 24 Apr 1999 | | Aldridge v Redditch | The Green, Aldridge | Results |
| 24 Apr 1999 | | Bedworth v Penn | Miners Welfare Park, Bedworth | Results |
| 24 Apr 1999 | | Kenilworth v Water Orton | Warwick Road, Kenilworth | Results |
| 24 Apr 1999 | | Studley v Evesham | Washford Fields, Studley | Results |
| 24 Apr 1999 | | Walmley v Pelsall | The John Findlay Memorial Ground, Walmley | Results |
| 24 Apr 1999 | | Worcester Norton Taverners v Moseley Ashfield | Brockhill Lane, Norton | Results |
| 01 May 1999 | | Lichfield v Moseley Ashfield | Collins Hill, Lichfield | Results |
| 01 May 1999 | | Pelsall v Bedworth | Walsall Road, Pelsall | Results |
| 01 May 1999 | | Penn v Worcester Norton Taverners | Mount Road, Penn | Results |
| 01 May 1999 | | Water Orton v Walmley | Coleshill Road, Water Orton | Results |
| 01 May 1999 | | Evesham v Aldridge | Evesham Sports Club Ground, Evesham | Results |
| 03 May 1999 | | Penn v Lichfield | Mount Road, Penn | Results |
| 03 May 1999 | | Studley v Moseley Ashfield | Washford Fields, Studley | Results |
| 03 May 1999 | | Walmley v Bedworth | The John Findlay Memorial Ground, Walmley | Results |
| 03 May 1999 | | Water Orton v Redditch | Coleshill Road, Water Orton | Results |
| 03 May 1999 | | Worcester Norton Taverners v Pelsall | Brockhill Lane, Norton | Results |
| 08 May 1999 | | Bedworth v Worcester Norton Taverners | Miners Welfare Park, Bedworth | Results |
| 08 May 1999 | | Evesham v Water Orton | Evesham Sports Club Ground, Evesham | Results |
| 08 May 1999 | | Lichfield v Pelsall | Collins Hill, Lichfield | Results |
| 08 May 1999 | | Moseley Ashfield v Aldridge | Yardley Wood Road, Moseley | Results |
| 08 May 1999 | | Penn v Studley | Mount Road, Penn | Results |
| 08 May 1999 | | Redditch v Walmley | Bromsgrove Road, Redditch | Results |
| 15 May 1999 | | Aldridge v Penn | The Green, Aldridge | Results |
| 15 May 1999 | | Bedworth v Lichfield | Miners Welfare Park, Bedworth | Results |
| 15 May 1999 | | Pelsall v Studley | Walsall Road, Pelsall | Results |
| 15 May 1999 | | Redditch v Evesham | Bromsgrove Road, Redditch | Results |
| 15 May 1999 | | Walmley v Worcester Norton Taverners | The John Findlay Memorial Ground, Walmley | Results |
| 22 May 1999 | | Evesham v Walmley | Evesham Sports Club Ground, Evesham | Results |
| 22 May 1999 | | Moseley Ashfield v Water Orton | Yardley Wood Road, Moseley | Results |
| 22 May 1999 | | Pelsall v Aldridge | Walsall Road, Pelsall | Results |
| 22 May 1999 | | Studley v Bedworth | Washford Fields, Studley | Results |
| 22 May 1999 | | Worcester Norton Taverners v Lichfield | Brockhill Lane, Norton | Results |
| 29 May 1999 | | Aldridge v Bedworth | The Green, Aldridge | Results |
| 29 May 1999 | | Redditch v Moseley Ashfield | Bromsgrove Road, Redditch | Results |
| 29 May 1999 | | Studley v Worcester Norton Taverners | Washford Fields, Studley | Results |
| 29 May 1999 | | Walmley v Lichfield | The John Findlay Memorial Ground, Walmley | Results |
| 29 May 1999 | | Water Orton v Penn | Coleshill Road, Water Orton | Results |
| 31 May 1999 | | Evesham v Moseley Ashfield | Evesham Sports Club Ground, Evesham | Results |
| 31 May 1999 | | Lichfield v Studley | Collins Hill, Lichfield | Results |
| 31 May 1999 | | Pelsall v Water Orton | Walsall Road, Pelsall | Results |
| 31 May 1999 | | Penn v Redditch | Mount Road, Penn | Results |
| 31 May 1999 | | Worcester Norton Taverners v Aldridge | Brockhill Lane, Norton | Results |
| 05 Jun 1999 | | Aldridge v Lichfield | The Green, Aldridge | Results |
| 05 Jun 1999 | | Penn v Evesham | Mount Road, Penn | Results |
| 05 Jun 1999 | | Redditch v Pelsall | Bromsgrove Road, Redditch | Results |
| 05 Jun 1999 | | Studley v Walmley | Washford Fields, Studley | Results |
| 05 Jun 1999 | | Water Orton v Bedworth | Coleshill Road, Water Orton | Results |
| 12 Jun 1999 | | Bedworth v Redditch | Miners Welfare Park, Bedworth | Results |
| 12 Jun 1999 | | Moseley Ashfield v Walmley | Yardley Wood Road, Moseley | Results |
| 12 Jun 1999 | | Pelsall v Evesham | Walsall Road, Pelsall | Results |
| 12 Jun 1999 | | Studley v Aldridge | Washford Fields, Studley | Results |
| 12 Jun 1999 | | Worcester Norton Taverners v Water Orton | Brockhill Lane, Norton | Results |
| 19 Jun 1999 | | Evesham v Bedworth | Evesham Sports Club Ground, Evesham | Results |
| 19 Jun 1999 | | Moseley Ashfield v Penn | Yardley Wood Road, Moseley | Results |
| 19 Jun 1999 | | Redditch v Worcester Norton Taverners | Bromsgrove Road, Redditch | Results |
| 19 Jun 1999 | | Walmley v Aldridge | The John Findlay Memorial Ground, Walmley | Results |
| 19 Jun 1999 | | Water Orton v Lichfield | Coleshill Road, Water Orton | Results |
| 26 Jun 1999 | | Lichfield v Redditch | Collins Hill, Lichfield | Results |
| 26 Jun 1999 | | Pelsall v Moseley Ashfield | Walsall Road, Pelsall | Results |
| 26 Jun 1999 | | Penn v Walmley | Mount Road, Penn | Results |
| 26 Jun 1999 | | Studley v Water Orton | Washford Fields, Studley | Results |
| 26 Jun 1999 | | Worcester Norton Taverners v Evesham | Brockhill Lane, Norton | Results |
| 03 Jul 1999 | | Aldridge v Water Orton | The Green, Aldridge | Results |
| 03 Jul 1999 | | Bedworth v Moseley Ashfield | Miners Welfare Park, Bedworth | Results |
| 03 Jul 1999 | | Lichfield v Evesham | Collins Hill, Lichfield | Results |
| 03 Jul 1999 | | Pelsall v Penn | Walsall Road, Pelsall | Results |
| 03 Jul 1999 | | Studley v Redditch | Washford Fields, Studley | Results |
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