diff --git a/library/std/src/path.rs b/library/std/src/path.rs
index caae8f924d2b1..2c140c1a14f40 100644
--- a/library/std/src/path.rs
+++ b/library/std/src/path.rs
@@ -3109,7 +3109,7 @@ impl Hash for Path {
                     bytes_hashed += to_hash.len();
                 }
 
-                // skip over separator and optionally a following CurDir item
+                // Skip over separators and, optionally, a following CurDir item
                 // since components() would normalize these away.
                 component_start = i + 1;
 
@@ -3117,9 +3117,22 @@ impl Hash for Path {
 
                 if !verbatim {
                     component_start += match tail {
+                        // At the end of the path, e.g. `foo/`
+                        [] => 0,
+                        // At the end of the path followed by a CurDir component, e.g. `foo/.`
                         [b'.'] => 1,
+                        // Followed by a CurDir component, another separator, and a component e.g. `foo/./bar`
                         [b'.', sep @ _, ..] if is_sep_byte(*sep) => 1,
-                        _ => 0,
+                        // Followed by another separator and a component, e.g. `foo//bar`
+                        [sep @ _, ..] if is_sep_byte(*sep) => 1,
+                        // Otherwise, it's a separator followed by a new component, e.g. `foo/bar`
+                        // and we should hash the separator to distinguish from `foobar`
+                        _ => {
+                            let to_hash = &[b'/' as u8];
+                            h.write(to_hash);
+                            bytes_hashed += to_hash.len();
+                            0
+                        }
                     };
                 }
             }
diff --git a/library/std/src/path/tests.rs b/library/std/src/path/tests.rs
index 92702b395dfe1..87a06a9ea9153 100644
--- a/library/std/src/path/tests.rs
+++ b/library/std/src/path/tests.rs
@@ -1545,6 +1545,20 @@ pub fn test_compare() {
     relative_from: Some("")
     );
 
+    tc!("foo//", "foo",
+    eq: true,
+    starts_with: true,
+    ends_with: true,
+    relative_from: Some("")
+    );
+
+    tc!("foo///", "foo",
+    eq: true,
+    starts_with: true,
+    ends_with: true,
+    relative_from: Some("")
+    );
+
     tc!("foo/.", "foo",
     eq: true,
     starts_with: true,
@@ -1559,6 +1573,20 @@ pub fn test_compare() {
     relative_from: Some("")
     );
 
+    tc!("foo/.//bar", "foo/bar",
+    eq: true,
+    starts_with: true,
+    ends_with: true,
+    relative_from: Some("")
+    );
+
+    tc!("foo//./bar", "foo/bar",
+    eq: true,
+    starts_with: true,
+    ends_with: true,
+    relative_from: Some("")
+    );
+
     tc!("foo/bar", "foo",
     eq: false,
     starts_with: true,
@@ -1566,6 +1594,13 @@ pub fn test_compare() {
     relative_from: Some("bar")
     );
 
+    tc!("foo/bar", "foobar",
+    eq: false,
+    starts_with: false,
+    ends_with: false,
+    relative_from: None
+    );
+
     tc!("foo/bar/baz", "foo/bar",
     eq: false,
     starts_with: true,