 | Date | Time | DTG | Location | | Match | Rink | | Score | Ends | Sheet |
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| 1. | Mon | 05 Oct | 20:30 | | Kinross | | Development Friendly | | Archie Rintoul vs Fossoway | 7 - 4 | 5 - 2 | D |
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| 2. | Wed | 07 Oct | 17:45 | | Kinross | | KCT League 1 | | Steve Jamieson v Kinross (19-20 season) | 7 - 5 | 4 - 3 | D |
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| 3. | Tue | 13 Oct | 17:45 | | Kinross | | Other | | ***** Trial Evening | - | - | D |
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| 4. | Thu | 15 Oct | 20:30 | | Kinross | | Dave Thomson League | 2 v 3 | Bob Tait vs Steve Jamieson | 4 - 6 | 3 - 4 | D |
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| 5. | Fri | 16 Oct | 17:45 | | Kinross | | Dave Thomson League | 1 v 3 | Jim Stuart vs Steve Jamieson | 5 - 3 | 4 - 3 | B |
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| 6. | Mon | 19 Oct | 20:30 | | Kinross | | Development Friendly | | Bill Brown vs Orwell Ladies | 4 - 5 | 3 - 4 | D |
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| 7. | Tue | 20 Oct | 12:15 | | Kinross | | Coaching | | Steve Jamieson with David MacGowan | - | - | C |
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| 8. | Tue | 20 Oct | 20:30 | | Kinross | | Dave Thomson League | 2 v 4 | Bob Tait vs Bill Linton | 5 - 5 | 3 - 4 | C |
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| 9. | Wed | 21 Oct | 17:45 | | Kinross | | KCT League 3 | | Tom Mitchell vs Aberdour (2019/20 Season) | 9 - 8 | 4 - 4 | D |
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| 10. | Fri | 23 Oct | 17:45 | | Kinross | | League Cup | 2 v 3 | Jim Anderson vs Bill Rennie | 1 - 10 | 1 - 6 | B |
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| 11. | Fri | 23 Oct | 20:30 | | Perth | | League Cup | 1 v 4 | Tom Mitchell vs Scott Mitchell | 6 - 3 | 6 - 2 | E |
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| 12. | Mon | 26 Oct | 17:45 | | Kinross | | Pairs | | Mike Caffyn vs Bill RennieRnd1 1 vs 2 | 4 - 2 | 3 - 2 | A |
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| 13. | Tue | 27 Oct | 20:30 | | Perth | | Lomond League | | Steve Jamieson vs Kinross | 6 - 1 | 6 - 1 | D |
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| 14. | Tue | 27 Oct | 20:30 | | Kinross | | Pairs | | Eddie Morrison vs Scott MitchellRnd1 3 vs 4 | 5 - 7 | 2 - 3 | A |
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| 15. | Wed | 28 Oct | 09:30 | | Kinross | | Coaching | | Steve Jamieson with David MacGowan | - | - | B |
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| 16. | Thu | 29 Oct | 20:30 | | Kinross | | Pairs | | Tom Mitchell vs David LintonRnd1 5 vs 6 | 3 - 2 | 3 - 2 | A |
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| 17. | Fri | 30 Oct | 17:45 | | Kinross | | Development Friendly | | John MacGalloway vs Glenfarg Ladies | - | - | D |
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| 18. | Mon | 02 Nov | 12:15 | | Kinross | | Dave Thomson League | 3 v 4 | Steve Jamieson vs Bill Linton | 2 - 9 | 2 - 5 | B |
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| 19. | Wed | 04 Nov | 20:30 | | Kinross | | KCT League 1 | | Bill Linton vs Kinross Juniors | 4 - 12 | 3 - 5 | A |
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| 20. | Fri | 06 Nov | 20:30 | | Perth | | Bill Kidd League | 2 v 3 | Ian Shaw vs Allan Brown | 7 - 5 | 5 - 3 | B |
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| 21. | Fri | 06 Nov | 20:30 | | Perth | | Bill Kidd League | 1 v 4 | Archie Rintoul vs Iain J Shaw | 6 - 8 | 4 - 4 | C |
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| 22. | Sat | 07 Nov | 09:30 | | Kinross | | JS Double Rink KO | | Steve Jamieson 2 John Stewart KO v Fossoway | 9 - 3 | 4 - 3 | B |
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| 23. | Sat | 07 Nov | 09:30 | | Kinross | | JS Double Rink KO | | Bob Tait 1 John Stewart KO v Fossoway | 11 - 5 | 4 - 3 | A |
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| 24. | Mon | 09 Nov | 09:30 | | Kinross | | Coaching | | Steve Jamieson with David MacGowan | - | - | D |
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| 25. | Mon | 09 Nov | 20:30 | | Kinross | | Challenge | | Bill Linton 2 vs Aberdour (Bill Rennie) | 9 - 6 | 5 - 2 | C |
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| 26. | Mon | 09 Nov | 20:30 | | Kinross | | Challenge | | Bob Tait 1 vs Aberdour (John Taddei) | 4 - 7 | 2 - 5 | D |
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| 27. | Tue | 10 Nov | 18:00 | | Perth | | Lomond League | | Bill Linton vs Glenfarg | 11 - 6 | 4 - 3 | B |
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| 28. | Wed | 11 Nov | 12:15 | | Kinross | | Other | | Steve Jamieson - practice game for Dave MacGowan | 11 - 3 | 5 - 2 | B |
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| 29. | Wed | 11 Nov | 12:15 | | Kinross | | Other | | Ian Baker - practice game for Dave MacGowan | 3 - 11 | 2 - 5 | B |
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| 30. | Wed | 11 Nov | 17:45 | | Kinross | | Pairs | | Eddie Morrison vs Jim StuartRnd 1 - 7 vs 8 | 4 - 2 | 3 - 2 | A |
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