Does it matter what time of day that I apply timolol drops?

No, but try to stick to putting them in 12 hrs apart, however, how you put the drop in matters a LOT.
Instil drop and keep eye(s) closed for 2 min (minimum) and pinch nose next to eye. This stops eye drop leaving the eye via the tear duct. Keep eyes closed for the entire 2 min..Dr's recommend 5 min. 5 min in the morning seems like a real real long time..At night it's easy, go to bed instil the drop and go to sleep holding your nose for a few minutes..Problem solved :-)