As queuesef pointed out above, your problem is that the dates/times you have are actually text, not dates/times as Excel understands them. The easiest way to deal with this is to first convert them to actual dates/times and then to do the calculation. To do this, add two 'helper' columns - insert new columns C and D between your current columns B and C. Then put this in the new C2:
Formula:
=DATE(--MID(A2,7,4),--LEFT(A2,2),--MID(A2,4,2))+TIME(--MID(A2,12,2),--RIGHT(A2,2),0)
Then this in the new D2:
Formula:
=IFERROR(DATE(--MID(B2,7,4),--LEFT(B2,2),--MID(B2,4,2))+TIME(--MID(B2,12,2),--RIGHT(B2,2),0),"")
Drag down both columns.
Note that both formulae assume that the text-formatted dates/times are always formatted as mm/dd/yyyy[space]hh:mm - in other words, with two-digit months and days, and using the American mm/dd format not the international dd/mm format.
Now the calculation in Col E (your old Col C) is fairly simple - subtract one time from the other, using an IF formula to check which time is later. The formula below will return just the time difference if the actual departure is later or equal to the scheduled, and will add ' early' if the actual time is earlier. Format the column with the custom number format [h]:mm.
Formula:
=IFERROR(IF(D2>=C2,D2-C2,TEXT(C2-D2,"[h]:mm")&" early"),"")
Note that the formula above changes the figure to text if the dep. was early, so if you want to do calculations with the numbers, it might be better to just have the number (i.e. the time diff) and put another column to note whether the actual dep is earlier or later. Put these two formulae in E2 and F2, then drag down.
Formula:
=IFERROR(IF(D2>=C2,D2-C2,C2-D2),"")
=IF(D2="","",IF(D2=C2,"on time",IF(D2>C2,"late","early")))
Hope that helps. Attached is a file showing it working - two sheets, with the two options for showing late/early.
Bookmarks