No, the order in which you pick up items doesn't matter.
If you don't believe me, let's do some Math!
Now, I can't find the current formula used in Rebirth, but I think that we can still rely on the original Binding of Isaac damage calculation.
In the previous version of the game, the damage formula was something like:
Effective Damage = Damage_Multiplier * (1 + 1.2 * Basic_Damage)^1/2
Each character starts with a base damage of 3.5 multiplied by a character-specific multiplier, for the sake of simplicity we can use 3.5. And we can forget the square root.
Every multiplicative bonus affects Damage_Multiplier, every additive bonus affects Basic_Damage.
For example, Cricket Head gives you:
+0.5 Damage up
x1.5 Damage multiplier
1.5 * (1 + 1.2 * (3.5 + 0.5)) = 8.7
Small Rock instead gives you +1 damage,
1.5 * (1 + 1.2 * (3.5 + 0.5 + 1)) = 10.5
You can see that the result is not affected by the order in which you get an item.