Timbers did league leaders Edinburgh Caledonian a huge favour in their bid to lift back-to-back league titles, given Caley remain five points clear with a game in hand over Vittoria.
Second placed Vittoria had taken a first half lead on the half hour mark from the penalty spot, but three goals after the interval secured Timbers an unexpected three points.
Timbers centre back Ryan Pollock equalised after 55 minutes in spectacular fashion when his cross cum shot from wide right landed in the top corner for his first goal of the campaign.
Substitute left winger Daniel Laing came off the bench to secure the three points with a late double - his first coming with ten minutes to spare when he netted after a solo run, before he sealed the comeback win in injury time.
Meadowmill AFC will face Meadowbank Wednesday in the final of the Sunday Morning Division 2 League Cup after they edged past Edinburgh City 2-1 on home soil to stretch their unbeaten run to eleven games.
With a big crowd in attendance, Meadowmill got the opener with three minutes left in the first half as Kyle Baker netted from a free-kick on the edge of the box.
Six minutes into the second half and Meadowmill were celebrating once again when Robbie Menzies’ deflected free-kick finding its way past City’s goalkeeper.
City pulled a goal back late on, but Meadowmill held firm to hold on to their slim advantage.
Elsewhere, Tollcross Thistle lifted the Centenary Cup with a 1-0 victory over Linlithgow Thistle which came courtesy of Stewart O’Neill’s fourth minute effort in a game of few chances.
Newcraighall Leith Vics leapfrogged Blackridge Vale of Craig in the Championship table with a 4-0 win over them, thanks to a Gordan Ramsay hat-trick and Tadg Moriarty strike.
It was a celebration for veteran Moriarty because, over the weekend, he was announced as manager for Newcraighall next season, stepping up from captain.