diff --git a/modules/caddyhttp/matchers.go b/modules/caddyhttp/matchers.go
index 93a36237b..7f62bdd3a 100644
--- a/modules/caddyhttp/matchers.go
+++ b/modules/caddyhttp/matchers.go
@@ -941,7 +941,7 @@ func (m *MatchHeader) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
 // Match returns true if r matches m.
 func (m MatchHeader) Match(r *http.Request) bool {
 	repl := r.Context().Value(caddy.ReplacerCtxKey).(*caddy.Replacer)
-	return matchHeaders(r.Header, http.Header(m), r.Host, repl)
+	return matchHeaders(r.Header, http.Header(m), r.Host, r.TransferEncoding, repl)
 }
 
 // CELLibrary produces options that expose this matcher for use in CEL
@@ -967,22 +967,26 @@ func (MatchHeader) CELLibrary(_ caddy.Context) (cel.Library, error) {
 }
 
 // getHeaderFieldVals returns the field values for the given fieldName from input.
-// The host parameter should be obtained from the http.Request.Host field since
-// net/http removes it from the header map.
-func getHeaderFieldVals(input http.Header, fieldName, host string) []string {
+// The host parameter should be obtained from the http.Request.Host field, and the
+// transferEncoding from http.Request.TransferEncoding, since net/http removes them
+// from the header map.
+func getHeaderFieldVals(input http.Header, fieldName, host string, transferEncoding []string) []string {
 	fieldName = textproto.CanonicalMIMEHeaderKey(fieldName)
 	if fieldName == "Host" && host != "" {
 		return []string{host}
 	}
+	if fieldName == "Transfer-Encoding" && input[fieldName] == nil {
+		return transferEncoding
+	}
 	return input[fieldName]
 }
 
 // matchHeaders returns true if input matches the criteria in against without regex.
 // The host parameter should be obtained from the http.Request.Host field since
 // net/http removes it from the header map.
-func matchHeaders(input, against http.Header, host string, repl *caddy.Replacer) bool {
+func matchHeaders(input, against http.Header, host string, transferEncoding []string, repl *caddy.Replacer) bool {
 	for field, allowedFieldVals := range against {
-		actualFieldVals := getHeaderFieldVals(input, field, host)
+		actualFieldVals := getHeaderFieldVals(input, field, host, transferEncoding)
 		if allowedFieldVals != nil && len(allowedFieldVals) == 0 && actualFieldVals != nil {
 			// a non-nil but empty list of allowed values means
 			// match if the header field exists at all
@@ -1076,7 +1080,7 @@ func (m *MatchHeaderRE) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
 // Match returns true if r matches m.
 func (m MatchHeaderRE) Match(r *http.Request) bool {
 	for field, rm := range m {
-		actualFieldVals := getHeaderFieldVals(r.Header, field, r.Host)
+		actualFieldVals := getHeaderFieldVals(r.Header, field, r.Host, r.TransferEncoding)
 		match := false
 	fieldVal:
 		for _, actualFieldVal := range actualFieldVals {
diff --git a/modules/caddyhttp/responsematchers.go b/modules/caddyhttp/responsematchers.go
index cf96b00cd..a6b34c76d 100644
--- a/modules/caddyhttp/responsematchers.go
+++ b/modules/caddyhttp/responsematchers.go
@@ -41,7 +41,7 @@ func (rm ResponseMatcher) Match(statusCode int, hdr http.Header) bool {
 	if !rm.matchStatusCode(statusCode) {
 		return false
 	}
-	return matchHeaders(hdr, rm.Headers, "", nil)
+	return matchHeaders(hdr, rm.Headers, "", []string{}, nil)
 }
 
 func (rm ResponseMatcher) matchStatusCode(statusCode int) bool {