diff --git a/fast-import.c b/fast-import.c
index 309f2c58a2..75ed738b7c 100644
--- a/fast-import.c
+++ b/fast-import.c
@@ -1528,6 +1528,14 @@ static int tree_content_remove(
 	for (i = 0; i < t->entry_count; i++) {
 		e = t->entries[i];
 		if (e->name->str_len == n && !strncmp(p, e->name->str_dat, n)) {
+			if (slash1 && !S_ISDIR(e->versions[1].mode))
+				/*
+				 * If p names a file in some subdirectory, and a
+				 * file or symlink matching the name of the
+				 * parent directory of p exists, then p cannot
+				 * exist and need not be deleted.
+				 */
+				return 1;
 			if (!slash1 || !S_ISDIR(e->versions[1].mode))
 				goto del_entry;
 			if (!e->tree)