By expanding the scope of your question, you can achieve the desired result: winning.
If Ebonblade Reaper is given Double Strike, and it deals combat damage to your opponent during both combat damage steps, you will win if the opponent has 20 or less life.
During the first combat damage step (ref: 510.5 and 702.4), Ebonblade Reaper deals 1 damage to the opponent, triggering both effects. AS the controller of both effects, you choose the order in which they enter the stack (inconsequential).
The last in resolves, your opponent has T-1 = X life, and they lose Y life, where Y = ceiling (X/2). X'= X - Y.
The second effect resolves, your opponent has X' life, and they lose Y' life, where Y'= ceiling (X'/2). X'' = X'-Y'
During the second combat damage step, Ebonblade Reaper deals 1 damage to the opponent.
The last in resolves, your opponent has X''-1 = M life, and they lose Y life, where Y = ceiling (X/2). M'= M - Y.
The second effect resolves, your opponent has X' life, and they lose Y' life, where Y'= ceiling (X'/2). M'' = M'-Y'
Now, a table of numbers demonstrating the results, for starting opponent life totals of (0,21).
T X X' X'' M M' M''
21 20 10 5 4 2 1
20 19 9 4 3 1 0
19 18 9 4 3 1 0
18 17 8 4 3 1 0
17 16 8 4 3 1 0
16 15 7 3 2 1 0
15 14 7 3 2 1 0
14 13 6 3 2 1 0
13 12 6 3 2 1 0
12 11 5 2 1 0 0
11 10 5 2 1 0 0
10 9 4 2 1 0 0
9 8 4 2 1 0 0
8 7 3 1 0 0 0
7 6 3 1 0 0 0
6 5 2 1 0 0 0
5 4 2 1 0 0 0
4 3 1 0 -1 -1 -1
3 2 1 0 -1 -1 -1
2 1 0 0 -1 -1 -1
1 0 0 0 -1 -1 -1
Now, you may be wondering about the -1's at the bottom of the table. The applicable rule is 107.1b:
107.1b Most of the time, the Magic game uses only positive numbers and zero. You can’t choose a negative number, deal negative damage, gain negative life, and so on. However, it’s possible for a game value, such as a creature’s power, to be less than zero. If a calculation or comparison needs to use a negative value, it does so. If a calculation that would determine the result of an effect yields a negative number, zero is used instead, unless that effect sets a player’s life total to a specific value, doubles a player’s life total, sets a creature’s power or toughness to a specific value, or otherwise modifies a creature’s power or toughness.
In the event there is an effect that prevents your opponent from losing with due to having 0 or less life, the game continues.
After the Ebonblade Reaper deals damage during the second combat damage step, for starting life totals (1,4) your opponent is at -1 life. Calculating the effect, the ceiling of (-1/2) is 0.
It becomes interesting if the life total before the effect is applied is -2. Since the effect is determining how much life the opponent will lose, rather than setting the life total to a specific value, if it determines a negative value, the result is 0 instead.
For example, with -2 life, the opponent loses half their life, rounded up.
(-2/2) = -1, rounded to -1. Rule 107.1b sees the negative value, and turns it into a 0.