I have compared them and it looks to be time related... somehow data in Wine is being shifted by 1 hour it seems, but not always, only around the weekends.
It almost seems like a Timezone issue even though both machines are set to the same GMT+1. The tested data was EURUSD, downloaded from zorro website, script was Workshop_4.

There are things like this all over the test.log
Wine:
[110: Fri 12-01-06 19:00] 1.2722/1.27261.2718/1.2722
[111: Sat 12-01-07 00:00] 1.2722/1.27311.2717/1.2720 <-- Saturday midnight?
[112: Sun 12-01-08 23:00] 1.2720/1.27201.2692/1.2694
[113: Mon 12-01-09 01:00] 1.2694/1.26941.2666/1.2689

Windows:
[110: Fri 12-01-06 19:00] 1.2722/1.27261.2718/1.2722
[111: Sun 12-01-08 23:00] 1.2722/1.27311.2692/1.2694
[112: Mon 12-01-09 00:00] 1.2694/1.26941.2666/1.2680
[113: Mon 12-01-09 01:00] 1.2680/1.26941.2678/1.2689