| 27 Apr 1929 | | Charlesworth v St Andrew's | Bankfield, Charlesworth | Results |
| 27 Apr 1929 | | Mottram v Hill End | Broadbottom Road, Mottram | Results |
| 27 Apr 1929 | | Ashton Trafalgar Square v Dinting | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 27 Apr 1929 | | Hollingworth v Old Glossop | Thorncliffe Hall Road, Hollingworth | Results |
| 27 Apr 1929 | | Glossop Second XI v Tintwistle | North Road, Glossop | Results |
| 04 May 1929 | | St Andrew's v Glossop Second XI | Pheasantford | Results |
| 04 May 1929 | | Old Glossop v Ashton Trafalgar Square | Manor Park Road, Glossop | Results |
| 04 May 1929 | | Dinting v Hill End | Simmondley Lane, Dinting | Results |
| 04 May 1929 | | Charlesworth v Hollingworth | Bankfield, Charlesworth | Results |
| 04 May 1929 | | Tintwistle v Mottram | Speedwell Park, Tintwistle | Results |
| 11 May 1929 | | Mottram v Hollingworth | Broadbottom Road, Mottram | Results |
| 11 May 1929 | | Tintwistle v Ashton Trafalgar Square | Speedwell Park, Tintwistle | Results |
| 11 May 1929 | | Hill End v Glossop Second XI | Hill End, Broadbottom | Results |
| 11 May 1929 | | Dinting v St Andrew's | Simmondley Lane, Dinting | Results |
| 11 May 1929 | | Old Glossop v Charlesworth | Manor Park Road, Glossop | Results |
| 18 May 1929 | | St Andrew's v Old Glossop | Pheasantford | Results |
| 18 May 1929 | | Ashton Trafalgar Square v Mottram | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 18 May 1929 | | Hollingworth v Dinting | Thorncliffe Hall Road, Hollingworth | Results |
| 18 May 1929 | | Hill End v Tintwistle | Hill End, Broadbottom | Results |
| 18 May 1929 | | Glossop Second XI v Charlesworth | North Road, Glossop | Results |
| 24 May 1929 | | St Andrew's v Hollingworth | Pheasantford | Results |
| 24 May 1929 | | Glossop Second XI v Mottram | North Road, Glossop | Results |
| 24 May 1929 | | Dinting v Tintwistle | Simmondley Lane, Dinting | Results |
| 24 May 1929 | | Old Glossop v Hill End | Manor Park Road, Glossop | Results |
| 25 May 1929 | | Charlesworth v Ashton Trafalgar Square | Bankfield, Charlesworth | Results |
| 27 May 1929 | | Glossop v Glossop and District Cricket League | North Road, Glossop | Results |
| 01 Jun 1929 | | Mottram v Dinting | Broadbottom Road, Mottram | Results |
| 01 Jun 1929 | | Tintwistle v Old Glossop | Speedwell Park, Tintwistle | Results |
| 01 Jun 1929 | | Hill End v Charlesworth | Hill End, Broadbottom | Results |
| 01 Jun 1929 | | Ashton Trafalgar Square v St Andrew's | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 01 Jun 1929 | | Glossop Second XI v Hollingworth | North Road, Glossop | Results |
| 08 Jun 1929 | | St Andrew's v Hill End | Pheasantford | Results |
| 08 Jun 1929 | | Hollingworth v Ashton Trafalgar Square | Thorncliffe Hall Road, Hollingworth | Results |
| 08 Jun 1929 | | Charlesworth v Tintwistle | Bankfield, Charlesworth | Results |
| 08 Jun 1929 | | Glossop Second XI v Dinting | North Road, Glossop | Results |
| 08 Jun 1929 | | Old Glossop v Mottram | Manor Park Road, Glossop | Results |
| 15 Jun 1929 | | Dinting v Old Glossop | Simmondley Lane, Dinting | Results |
| 15 Jun 1929 | | Mottram v Charlesworth | Broadbottom Road, Mottram | Results |
| 15 Jun 1929 | | Tintwistle v St Andrew's | Speedwell Park, Tintwistle | Results |
| 15 Jun 1929 | | Hill End v Hollingworth | Hill End, Broadbottom | Results |
| 15 Jun 1929 | | Ashton Trafalgar Square v Glossop Second XI | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 22 Jun 1929 | | Old Glossop v Glossop Second XI | Manor Park Road, Glossop | Results |
| 22 Jun 1929 | | Dinting v Charlesworth | Simmondley Lane, Dinting | Results |
| 22 Jun 1929 | | Mottram v St Andrew's | Broadbottom Road, Mottram | Results |
| 22 Jun 1929 | | Hill End v Ashton Trafalgar Square | Hill End, Broadbottom | Results |
| 22 Jun 1929 | | Hollingworth v Tintwistle | Thorncliffe Hall Road, Hollingworth | Results |
| 29 Jun 1929 | | St Andrew's v Dinting | Pheasantford | Results |
| 29 Jun 1929 | | Charlesworth v Old Glossop | Bankfield, Charlesworth | Results |
| 29 Jun 1929 | | Ashton Trafalgar Square v Tintwistle | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 29 Jun 1929 | | Hollingworth v Mottram | Thorncliffe Hall Road, Hollingworth | Results |
| 29 Jun 1929 | | Glossop Second XI v Hill End | North Road, Glossop | Results |
| 06 Jul 1929 | | St Andrew's v Charlesworth | Pheasantford | Results |
| 06 Jul 1929 | | Old Glossop v Hollingworth | Manor Park Road, Glossop | Results |
| 06 Jul 1929 | | Dinting v Ashton Trafalgar Square | Simmondley Lane, Dinting | Results |
| 06 Jul 1929 | | Tintwistle v Glossop Second XI | Speedwell Park, Tintwistle | Results |
| 06 Jul 1929 | | Hill End v Mottram | Hill End, Broadbottom | Results |
| 13 Jul 1929 | | Tintwistle v Hill End | Speedwell Park, Tintwistle | Results |
| 13 Jul 1929 | | Mottram v Ashton Trafalgar Square | Broadbottom Road, Mottram | Results |
| 13 Jul 1929 | | Dinting v Hollingworth | Simmondley Lane, Dinting | Results |
| 13 Jul 1929 | | Old Glossop v St Andrew's | Manor Park Road, Glossop | Results |
| 13 Jul 1929 | | Charlesworth v Glossop Second XI | Bankfield, Charlesworth | Results |
| 20 Jul 1929 | | Mottram v Tintwistle | Broadbottom Road, Mottram | Results |
| 20 Jul 1929 | | Hill End v Dinting | Hill End, Broadbottom | Results |
| 20 Jul 1929 | | Ashton Trafalgar Square v Old Glossop | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 20 Jul 1929 | | Hollingworth v Charlesworth | Thorncliffe Hall Road, Hollingworth | Results |
| 20 Jul 1929 | | Glossop Second XI v St Andrew's | North Road, Glossop | Results |
| 27 Jul 1929 | | Tintwistle v Hollingworth | Speedwell Park, Tintwistle | Results |
| 27 Jul 1929 | | St Andrew's v Mottram | Pheasantford | Results |
| 27 Jul 1929 | | Charlesworth v Dinting | Bankfield, Charlesworth | Results |
| 27 Jul 1929 | | Ashton Trafalgar Square v Hill End | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 27 Jul 1929 | | Glossop Second XI v Old Glossop | North Road, Glossop | Results |
| 03 Aug 1929 | | St Andrew's v Ashton Trafalgar Square | Pheasantford | Results |
| 03 Aug 1929 | | Charlesworth v Hill End | Bankfield, Charlesworth | Results |
| 03 Aug 1929 | | Old Glossop v Tintwistle | Manor Park Road, Glossop | Results |
| 03 Aug 1929 | | Dinting v Mottram | Simmondley Lane, Dinting | Results |
| 03 Aug 1929 | | Hollingworth v Glossop Second XI | Thorncliffe Hall Road, Hollingworth | Results |
| 10 Aug 1929 | | Ashton Trafalgar Square v Hollingworth | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 10 Aug 1929 | | Dinting v Glossop Second XI | Simmondley Lane, Dinting | Results |
| 10 Aug 1929 | | Mottram v Old Glossop | Broadbottom Road, Mottram | Results |
| 10 Aug 1929 | | Tintwistle v Charlesworth | Speedwell Park, Tintwistle | Results |
| 10 Aug 1929 | | Hill End v St Andrew's | Hill End, Broadbottom | Results |
| 31 Aug 1929 | | St Andrew's v Tintwistle | Pheasantford | Results |
| 31 Aug 1929 | | Charlesworth v Mottram | Bankfield, Charlesworth | Results |
| 31 Aug 1929 | | Old Glossop v Dinting | Manor Park Road, Glossop | Results |
| 31 Aug 1929 | | Hollingworth v Hill End | Thorncliffe Hall Road, Hollingworth | Results |
| 31 Aug 1929 | | Glossop Second XI v Ashton Trafalgar Square | North Road, Glossop | Results |
| 07 Sep 1929 | | Hollingworth v St Andrew's | Thorncliffe Hall Road, Hollingworth | Results |
| 07 Sep 1929 | | Ashton Trafalgar Square v Charlesworth | Ashton Trafalgar Square Cricket Club Ground, Ashton-under-Lyne | Results |
| 07 Sep 1929 | | Hill End v Old Glossop | Hill End, Broadbottom | Results |
| 07 Sep 1929 | | Tintwistle v Dinting | Speedwell Park, Tintwistle | Results |
| 07 Sep 1929 | | Mottram v Glossop Second XI | Broadbottom Road, Mottram | Results |
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