diff --git a/cli/command/image/build/context.go b/cli/command/image/build/context.go
index 5d0e96737d..e9af9bd358 100644
--- a/cli/command/image/build/context.go
+++ b/cli/command/image/build/context.go
@@ -41,6 +41,12 @@ func ValidateContextDirectory(srcPath string, excludes []string) error {
 	if err != nil {
 		return err
 	}
+
+	pm, err := fileutils.NewPatternMatcher(excludes)
+	if err != nil {
+		return err
+	}
+
 	return filepath.Walk(contextRoot, func(filePath string, f os.FileInfo, err error) error {
 		if err != nil {
 			if os.IsPermission(err) {
@@ -55,7 +61,7 @@ func ValidateContextDirectory(srcPath string, excludes []string) error {
 		// skip this directory/file if it's not in the path, it won't get added to the context
 		if relFilePath, err := filepath.Rel(contextRoot, filePath); err != nil {
 			return err
-		} else if skip, err := fileutils.Matches(relFilePath, excludes); err != nil {
+		} else if skip, err := filepathMatches(pm, relFilePath); err != nil {
 			return err
 		} else if skip {
 			if f.IsDir() {
@@ -81,6 +87,15 @@ func ValidateContextDirectory(srcPath string, excludes []string) error {
 	})
 }
 
+func filepathMatches(matcher *fileutils.PatternMatcher, file string) (bool, error) {
+	file = filepath.Clean(file)
+	if file == "." {
+		// Don't let them exclude everything, kind of silly.
+		return false, nil
+	}
+	return matcher.Matches(file)
+}
+
 // DetectArchiveReader detects whether the input stream is an archive or a
 // Dockerfile and returns a buffered version of input, safe to consume in lieu
 // of input. If an archive is detected, isArchive is set to true, and to false
diff --git a/cli/command/image/build/context_test.go b/cli/command/image/build/context_test.go
index e0922542e7..de4d38f75d 100644
--- a/cli/command/image/build/context_test.go
+++ b/cli/command/image/build/context_test.go
@@ -12,6 +12,7 @@ import (
 	"testing"
 
 	"github.com/docker/docker/pkg/archive"
+	"github.com/docker/docker/pkg/fileutils"
 	"gotest.tools/assert"
 	is "gotest.tools/assert/cmp"
 )
@@ -330,3 +331,86 @@ func TestDetectArchiveReader(t *testing.T) {
 		assert.Check(t, is.Equal(testcase.expected, isArchive), testcase.file)
 	}
 }
+
+func mustPatternMatcher(t *testing.T, patterns []string) *fileutils.PatternMatcher {
+	t.Helper()
+	pm, err := fileutils.NewPatternMatcher(patterns)
+	if err != nil {
+		t.Fatal("failed to construct pattern matcher: ", err)
+	}
+	return pm
+}
+
+func TestWildcardMatches(t *testing.T) {
+	match, _ := filepathMatches(mustPatternMatcher(t, []string{"*"}), "fileutils.go")
+	if !match {
+		t.Errorf("failed to get a wildcard match, got %v", match)
+	}
+}
+
+// A simple pattern match should return true.
+func TestPatternMatches(t *testing.T) {
+	match, _ := filepathMatches(mustPatternMatcher(t, []string{"*.go"}), "fileutils.go")
+	if !match {
+		t.Errorf("failed to get a match, got %v", match)
+	}
+}
+
+// An exclusion followed by an inclusion should return true.
+func TestExclusionPatternMatchesPatternBefore(t *testing.T) {
+	match, _ := filepathMatches(mustPatternMatcher(t, []string{"!fileutils.go", "*.go"}), "fileutils.go")
+	if !match {
+		t.Errorf("failed to get true match on exclusion pattern, got %v", match)
+	}
+}
+
+// A folder pattern followed by an exception should return false.
+func TestPatternMatchesFolderExclusions(t *testing.T) {
+	match, _ := filepathMatches(mustPatternMatcher(t, []string{"docs", "!docs/README.md"}), "docs/README.md")
+	if match {
+		t.Errorf("failed to get a false match on exclusion pattern, got %v", match)
+	}
+}
+
+// A folder pattern followed by an exception should return false.
+func TestPatternMatchesFolderWithSlashExclusions(t *testing.T) {
+	match, _ := filepathMatches(mustPatternMatcher(t, []string{"docs/", "!docs/README.md"}), "docs/README.md")
+	if match {
+		t.Errorf("failed to get a false match on exclusion pattern, got %v", match)
+	}
+}
+
+// A folder pattern followed by an exception should return false.
+func TestPatternMatchesFolderWildcardExclusions(t *testing.T) {
+	match, _ := filepathMatches(mustPatternMatcher(t, []string{"docs/*", "!docs/README.md"}), "docs/README.md")
+	if match {
+		t.Errorf("failed to get a false match on exclusion pattern, got %v", match)
+	}
+}
+
+// A pattern followed by an exclusion should return false.
+func TestExclusionPatternMatchesPatternAfter(t *testing.T) {
+	match, _ := filepathMatches(mustPatternMatcher(t, []string{"*.go", "!fileutils.go"}), "fileutils.go")
+	if match {
+		t.Errorf("failed to get false match on exclusion pattern, got %v", match)
+	}
+}
+
+// A filename evaluating to . should return false.
+func TestExclusionPatternMatchesWholeDirectory(t *testing.T) {
+	match, _ := filepathMatches(mustPatternMatcher(t, []string{"*.go"}), ".")
+	if match {
+		t.Errorf("failed to get false match on ., got %v", match)
+	}
+}
+
+// Matches with no patterns
+func TestMatchesWithNoPatterns(t *testing.T) {
+	matches, err := filepathMatches(mustPatternMatcher(t, []string{}), "/any/path/there")
+	if err != nil {
+		t.Fatal(err)
+	}
+	if matches {
+		t.Fatalf("Should not have match anything")
+	}
+}