Deveronvale left nine-man Montrose reeling after a late goal flurry put them into the next round of the cup.
Gerrard Stirling had given Montrose a 12th-minute lead and Greig Henslee doubled the advantage 10 minutes later. But Hugh Davidson was then red carded.
Montrose then lost Chris McLeod to a red card in 87 minutes.
Deveronvale hit back with a Mike McKenzie penalty. Scott Fraser then hit an equaliser before Michael Ewen completed a sensational comeback.
Deveronvale: Blanchard, Dolan, Gilbert, Chisholm, Scott Fraser, Brown, McWilliam (Watt 65), Smith, McKenzie, Murray, Urquhart (Ewen 73). Subs Not Used: Cowie, Bremner, Alexander.
Booked: Smith, Gilbert, Chisholm, Scott Fraser.
Goals: McKenzie 86 pen, Scott Fraser 90, Ewen 90.
Montrose: Andrew Reid, Cumming, Stirling, Michie, McLeod, Gibson, Henslee, Davidson, Rogers (Kerrigan 75), Mercer (Donachie 55), Campbell (Adam 46). Subs Not Used: Mackie, Farquhar.
Sent Off: Davidson (35), McLeod (76).
Booked: Davidson, Andrew Reid.
Goals: Stirling 11, Henslee 23.
Ref: S Nichols.