So I had a chain of conditional command blocks, and one of them had a /scoreboard that would set a players score to -2. That command worked in the chain, however, the command block after it would not trigger. I switched the score it set the player to positive 1 and the next command block did trigger. I also tried it with adding a score to a negative score, and unless it equaled at least 1, the next command block would not trigger
I wasn't able to reproduce this, even in 1.14.4. The conditional command block always executes regardless of the value to which the score is set.