diff --git a/arduino/cores/cores.go b/arduino/cores/cores.go
index 9b90bc84744..b5ce672c7b1 100644
--- a/arduino/cores/cores.go
+++ b/arduino/cores/cores.go
@@ -218,7 +218,7 @@ func (release *PlatformRelease) RequiresToolRelease(toolRelease *ToolRelease) bo
 	for _, toolDep := range release.Dependencies {
 		if toolDep.ToolName == toolRelease.Tool.Name &&
 			toolDep.ToolPackager == toolRelease.Tool.Package.Name &&
-			toolDep.ToolVersion == toolRelease.Version {
+			toolDep.ToolVersion.Equal(toolRelease.Version) {
 			return true
 		}
 	}
diff --git a/arduino/cores/cores_test.go b/arduino/cores/cores_test.go
new file mode 100644
index 00000000000..6df901ae230
--- /dev/null
+++ b/arduino/cores/cores_test.go
@@ -0,0 +1,57 @@
+// This file is part of arduino-cli.
+//
+// Copyright 2020 ARDUINO SA (http://www.arduino.cc/)
+//
+// This software is released under the GNU General Public License version 3,
+// which covers the main part of arduino-cli.
+// The terms of this license can be found at:
+// https://www.gnu.org/licenses/gpl-3.0.en.html
+//
+// You can be released from the requirements of the above licenses by purchasing
+// a commercial license. Buying such a license is mandatory if you want to
+// modify or otherwise use the software for commercial activities involving the
+// Arduino software without disclosing the source code of your own applications.
+// To purchase a commercial license, send an email to license@arduino.cc.
+
+package cores
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+	semver "go.bug.st/relaxed-semver"
+)
+
+func TestRequiresToolRelease(t *testing.T) {
+	toolDependencyName := "avr-gcc"
+	toolDependencyVersion := "7.3.0-atmel3.6.1-arduino7"
+	toolDependencyPackager := "arduino"
+
+	release := PlatformRelease{
+		Dependencies: ToolDependencies{
+			{
+				ToolName:     toolDependencyName,
+				ToolVersion:  semver.ParseRelaxed(toolDependencyVersion),
+				ToolPackager: toolDependencyPackager,
+			},
+		},
+	}
+
+	toolRelease := &ToolRelease{
+		Version: semver.ParseRelaxed(toolDependencyVersion + "not"),
+		Tool: &Tool{
+			Name: toolDependencyName + "not",
+			Package: &Package{
+				Name: toolDependencyPackager + "not",
+			},
+		},
+	}
+
+	require.False(t, release.RequiresToolRelease(toolRelease))
+	toolRelease.Tool.Name = toolDependencyName
+	require.False(t, release.RequiresToolRelease(toolRelease))
+	toolRelease.Tool.Package.Name = toolDependencyPackager
+	require.False(t, release.RequiresToolRelease(toolRelease))
+	toolRelease.Version = semver.ParseRelaxed(toolDependencyVersion)
+	require.True(t, release.RequiresToolRelease(toolRelease))
+}
diff --git a/test/test_core.py b/test/test_core.py
index 950f73265f2..6e3c28a163b 100644
--- a/test/test_core.py
+++ b/test/test_core.py
@@ -205,6 +205,27 @@ def test_core_uninstall(run_command):
     assert not _in(result.stdout, "arduino:avr")
 
 
+def test_core_uninstall_tool_dependency_removal(run_command, data_dir):
+    # These platforms both have a dependency on the arduino:avr-gcc@7.3.0-atmel3.6.1-arduino5 tool
+    # arduino:avr@1.8.2 has a dependency on arduino:avrdude@6.3.0-arduino17
+    assert run_command("core install arduino:avr@1.8.2")
+    # arduino:megaavr@1.8.4 has a dependency on arduino:avrdude@6.3.0-arduino16
+    assert run_command("core install arduino:megaavr@1.8.4")
+    assert run_command("core uninstall arduino:avr")
+
+    arduino_tools_path = Path(data_dir, "packages", "arduino", "tools")
+
+    avr_gcc_binaries_path = arduino_tools_path.joinpath("avr-gcc", "7.3.0-atmel3.6.1-arduino5", "bin")
+    # The tool arduino:avr-gcc@7.3.0-atmel3.6.1-arduino5 that is a dep of another installed platform should remain
+    assert avr_gcc_binaries_path.joinpath("avr-gcc").exists() or avr_gcc_binaries_path.joinpath("avr-gcc.exe").exists()
+
+    avrdude_binaries_path = arduino_tools_path.joinpath("avrdude", "6.3.0-arduino17", "bin")
+    # The tool arduino:avrdude@6.3.0-arduino17 that is only a dep of arduino:avr should have been removed
+    assert (
+        avrdude_binaries_path.joinpath("avrdude").exists() or avrdude_binaries_path.joinpath("avrdude.exe").exists()
+    ) is False
+
+
 def test_core_zipslip(run_command):
     url = "https://raw.githubusercontent.com/arduino/arduino-cli/master/test/testdata/test_index.json"
     assert run_command("core update-index --additional-urls={}".format(url))