diff --git a/diff.c b/diff.c
index 7c730fe6449..52c791574b7 100644
--- a/diff.c
+++ b/diff.c
@@ -2053,7 +2053,7 @@ static void fn_out_diff_words_aux(void *priv,
 static int find_word_boundaries(mmfile_t *buffer, regex_t *word_regex,
 		int *begin, int *end)
 {
-	if (word_regex && *begin < buffer->size) {
+	while (word_regex && *begin < buffer->size) {
 		regmatch_t match[1];
 		if (!regexec_buf(word_regex, buffer->ptr + *begin,
 				 buffer->size - *begin, 1, match, 0)) {
@@ -2061,9 +2061,13 @@ static int find_word_boundaries(mmfile_t *buffer, regex_t *word_regex,
 					'\n', match[0].rm_eo - match[0].rm_so);
 			*end = p ? p - buffer->ptr : match[0].rm_eo + *begin;
 			*begin += match[0].rm_so;
-			return *begin >= *end;
+			if (*begin == *end)
+				(*begin)++;
+			else
+				return *begin > *end;
+		} else {
+			return -1;
 		}
-		return -1;
 	}
 
 	/* find the next word */
diff --git a/t/t4034-diff-words.sh b/t/t4034-diff-words.sh
index ee7721ab913..561c582d161 100755
--- a/t/t4034-diff-words.sh
+++ b/t/t4034-diff-words.sh
@@ -184,6 +184,11 @@ test_expect_success 'word diff with a regular expression' '
 	word_diff --color-words="[a-z]+"
 '
 
+test_expect_success 'word diff with zero length matches' '
+	cp expect.letter-runs-are-words expect &&
+	word_diff --color-words="[a-z${LF}]*"
+'
+
 test_expect_success 'set up a diff driver' '
 	git config diff.testdriver.wordRegex "[^[:space:]]" &&
 	cat <<-\EOF >.gitattributes