diff --git a/python/openapi/src/com/jetbrains/python/packaging/requirement/PyRequirementVersionSpec.java b/python/openapi/src/com/jetbrains/python/packaging/requirement/PyRequirementVersionSpec.java
index 1d51b6bf3cbd..69b983dba2ad 100644
--- a/python/openapi/src/com/jetbrains/python/packaging/requirement/PyRequirementVersionSpec.java
+++ b/python/openapi/src/com/jetbrains/python/packaging/requirement/PyRequirementVersionSpec.java
@@ -99,7 +99,10 @@ public class PyRequirementVersionSpec {
       case NE:
         return VERSION_COMPARATOR.compare(version, myVersion) != 0;
       case COMPATIBLE:
-        return false; // TODO: implement matching version against compatible relation
+        Objects.requireNonNull(myParsedVersion);
+
+        return new PyRequirementVersionSpec(PyRequirementRelation.GTE, myParsedVersion).matches(version) &&
+               new PyRequirementVersionSpec(PyRequirementRelation.EQ, toEqPartOfCompatibleRelation(myParsedVersion)).matches(version);
       case STR_EQ:
         return version.equals(myVersion);
       default:
@@ -124,4 +127,14 @@ public class PyRequirementVersionSpec {
 
     return Pair.createNonNull(publicVersion, localVersion);
   }
+
+  @NotNull
+  private static PyRequirementVersion toEqPartOfCompatibleRelation(@NotNull PyRequirementVersion version) {
+    final String release = version.getRelease();
+    final int lastPoint = release.lastIndexOf(".");
+
+    if (lastPoint == -1) return version;
+
+    return new PyRequirementVersion(version.getEpoch(), release.substring(0, lastPoint) + "*", null, null, null, null);
+  }
 }
diff --git a/python/testSrc/com/jetbrains/python/packaging/PyRequirementTest.java b/python/testSrc/com/jetbrains/python/packaging/PyRequirementTest.java
index 024e31c477c7..f2935af155ec 100644
--- a/python/testSrc/com/jetbrains/python/packaging/PyRequirementTest.java
+++ b/python/testSrc/com/jetbrains/python/packaging/PyRequirementTest.java
@@ -2320,6 +2320,46 @@ public class PyRequirementTest extends PyTestCase {
     assertEquals(negativeLocalVersion, negativeRequirement.match(Collections.singletonList(negativeLocalVersion)));
   }
 
+  // https://www.python.org/dev/peps/pep-0440/#compatible-release
+  // PY-20522
+  public void testMatchingCompatible() {
+    final PyRequirement requirement = PyRequirement.fromLine("foo~=2.2");
+    final PyPackage release = new PyPackage("foo", "2.3", null, Collections.emptyList());
+    final PyPackage pre = new PyPackage("foo", "2.3a1", null, Collections.emptyList());
+    final PyPackage post = new PyPackage("foo", "2.3.post1", null, Collections.emptyList());
+    final PyPackage dev = new PyPackage("foo", "2.3.dev1", null, Collections.emptyList());
+    final PyPackage localVersion = new PyPackage("foo", "2.3+local.version", null, Collections.emptyList());
+
+    assertEquals(release, requirement.match(Collections.singletonList(release)));
+    assertEquals(pre, requirement.match(Collections.singletonList(pre)));
+    assertEquals(post, requirement.match(Collections.singletonList(post)));
+    assertEquals(dev, requirement.match(Collections.singletonList(dev)));
+    assertEquals(localVersion, requirement.match(Collections.singletonList(localVersion)));
+
+    final PyRequirement moreModernRequirement = PyRequirement.fromLine("foo~=2.4");
+    assertNull(moreModernRequirement.match(Arrays.asList(release, pre, post, dev, localVersion)));
+  }
+
+  // https://www.python.org/dev/peps/pep-0440/#compatible-release
+  // PY-20522
+  public void testMatchingCompatibleWithTrailingZero() {
+    final PyRequirement requirement = PyRequirement.fromLine("foo~=2.20.0");
+    final PyPackage release = new PyPackage("foo", "2.20.3", null, Collections.emptyList());
+    final PyPackage pre = new PyPackage("foo", "2.20.3a1", null, Collections.emptyList());
+    final PyPackage post = new PyPackage("foo", "2.20.3.post1", null, Collections.emptyList());
+    final PyPackage dev = new PyPackage("foo", "2.20.3.dev1", null, Collections.emptyList());
+    final PyPackage localVersion = new PyPackage("foo", "2.20.3+local.version", null, Collections.emptyList());
+
+    assertEquals(release, requirement.match(Collections.singletonList(release)));
+    assertEquals(pre, requirement.match(Collections.singletonList(pre)));
+    assertEquals(post, requirement.match(Collections.singletonList(post)));
+    assertEquals(dev, requirement.match(Collections.singletonList(dev)));
+    assertEquals(localVersion, requirement.match(Collections.singletonList(localVersion)));
+
+    final PyRequirement moreModernRequirement = PyRequirement.fromLine("foo~=2.21.0");
+    assertNull(moreModernRequirement.match(Arrays.asList(release, pre, post, dev, localVersion)));
+  }
+
   // OPTIONS
   public void testOptions() {
     assertEmpty(