| 30 Jul 22 | r01   | FalkirkFalkirk | 0 - 0 | MontroseMontrose |
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| 06 Aug 22 | r02 | MontroseMontrose | 0 - 0 | Queen of SouthQueen of Sout |
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| 13 Aug 22 | r03 | DunfermlineDunfermline | 1 - 0 | MontroseMontrose |
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| 20 Aug 22 | r04 | MontroseMontrose | 2 - 1 | ClydeClyde |
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| 27 Aug 22 | r05 | MontroseMontrose | 3 - 0 | Kelty HeartsKelty Hearts |
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| 03 Sep 22 | r06 | Peterhead FCPeterhead FC | 0 - 2 | MontroseMontrose |
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| 17 Sep 22 | r08 | AlloaAlloa | 2 - 1 | MontroseMontrose |
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| 01 Oct 22 | r09 | MontroseMontrose | 1 - 2 | Edinburgh CityEdinburgh Cit |
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| 04 Oct 22 | r07 | MontroseMontrose | 4 - 2 | AirdrieoniansAirdrieonians |
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| 08 Oct 22 | r10 | ClydeClyde | 1 - 3 | MontroseMontrose |
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| 15 Oct 22 | r11 | MontroseMontrose | 1 - 1 | FalkirkFalkirk |
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| 22 Oct 22 | r12 | MontroseMontrose | 2 - 0 | DunfermlineDunfermline |
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| 29 Oct 22 | r13 | AirdrieoniansAirdrieonians | 4 - 0 | MontroseMontrose |
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| 05 Nov 22 | r14 | MontroseMontrose | 3 - 0 | Peterhead FCPeterhead FC |
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| 12 Nov 22 | r15 | Kelty HeartsKelty Hearts | 1 - 3 | MontroseMontrose |
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| 19 Nov 22 | r16 | Queen of SouthQueen of Sout | 4 - 0 | MontroseMontrose |
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| 03 Dec 22 | r17 | MontroseMontrose | 0 - 0 | AlloaAlloa |
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| 17 Dec 22 | r18 | Edinburgh CityEdinburgh Cit | 2 - 2 | MontroseMontrose |
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| 23 Dec 22 | r19 | MontroseMontrose | 2 - 4 | AirdrieoniansAirdrieonians |
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| 02 Jan 23 | r20 | Peterhead FCPeterhead FC | 0 - 0 | MontroseMontrose |
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| 07 Jan 23 | r21 | FalkirkFalkirk | 2 - 1 | MontroseMontrose |
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| 14 Jan 23 | r22 | MontroseMontrose | 1 - 0 | Queen of SouthQueen of Sout |
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| 28 Jan 23 | r23 | MontroseMontrose | 3 - 3 | Kelty HeartsKelty Hearts |
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| 04 Feb 23 | r24 | DunfermlineDunfermline | 2 - 0 | MontroseMontrose |
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| 18 Feb 23 | r25 | MontroseMontrose | 3 - 3 | Edinburgh CityEdinburgh Cit |
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| 25 Feb 23 | r26 | AlloaAlloa | 1 - 0 | MontroseMontrose |
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| 04 Mar 23 | r27 | MontroseMontrose | 2 - 0 | ClydeClyde |
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| 18 Mar 23 | r29 | Kelty HeartsKelty Hearts | 1 - 2 | MontroseMontrose |
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| 25 Mar 23 | r30 | MontroseMontrose | 1 - 3 | DunfermlineDunfermline |
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| 01 Apr 23 | r31 | Edinburgh CityEdinburgh Cit | 1 - 1 | MontroseMontrose |
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| 08 Apr 23 | r32 | AirdrieoniansAirdrieonians | 3 - 0 | MontroseMontrose |
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| 11 Apr 23 | r28 | MontroseMontrose | 1 - 2 | FalkirkFalkirk |
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| 15 Apr 23 | r33 | MontroseMontrose | 2 - 1 | Peterhead FCPeterhead FC |
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| 22 Apr 23 | r34 | Queen of SouthQueen of Sout | 2 - 3 | MontroseMontrose |
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| 29 Apr 23 | r35 | MontroseMontrose | 0 - 4 | AlloaAlloa |
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| 06 May 23 | r36 | ClydeClyde | 2 - 1 | MontroseMontrose |
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