diff --git a/CHANGELOG.asciidoc b/CHANGELOG.asciidoc
index b477c13d343..ff15f812ff6 100644
--- a/CHANGELOG.asciidoc
+++ b/CHANGELOG.asciidoc
@@ -142,6 +142,7 @@ https://github.com/elastic/beats/compare/v5.2.2...v5.3.0[View commits]
 - Update regular expressions used for matching file names or lines (multiline, include/exclude functionality) to new matchers improving performance of simple string matches. {pull}3469[3469]
 - The `symlinks` and `harverster_limit` settings are now GA, instead of experimental. {pull}3525[3525]
 - close_timeout is also applied when the output is blocking. {pull}3511[3511]
+- Improve handling of different path variants on Windows. {pull}3781[3781]
 
 
 *Metricbeat*
diff --git a/filebeat/prospector/prospector_log.go b/filebeat/prospector/prospector_log.go
index 6e50778fde8..e696e30af3a 100644
--- a/filebeat/prospector/prospector_log.go
+++ b/filebeat/prospector/prospector_log.go
@@ -5,8 +5,6 @@ import (
 	"fmt"
 	"os"
 	"path/filepath"
-	"runtime"
-	"strings"
 	"time"
 
 	"github.com/elastic/beats/filebeat/harvester"
@@ -180,13 +178,14 @@ func (p *ProspectorLog) getFiles() map[string]os.FileInfo {
 
 // matchesFile returns true in case the given filePath is part of this prospector, means matches its glob patterns
 func (p *ProspectorLog) matchesFile(filePath string) bool {
+
+	// Path is cleaned to ensure we always compare clean paths
+	filePath = filepath.Clean(filePath)
+
 	for _, glob := range p.config.Paths {
 
-		if runtime.GOOS == "windows" {
-			// Windows allows / slashes which makes glob patterns with / work
-			// But for match we need paths with \ as only file names are compared and no lookup happens
-			glob = strings.Replace(glob, "/", "\\", -1)
-		}
+		// Glob is cleaned to ensure we always compare clean paths
+		glob = filepath.Clean(glob)
 
 		// Evaluate if glob matches filePath
 		match, err := filepath.Match(glob, filePath)
diff --git a/filebeat/prospector/prospector_log_windows_test.go b/filebeat/prospector/prospector_log_windows_test.go
index 213d35a11af..14f67f0a66d 100644
--- a/filebeat/prospector/prospector_log_windows_test.go
+++ b/filebeat/prospector/prospector_log_windows_test.go
@@ -16,14 +16,38 @@ var matchTestsWindows = []struct {
 	result       bool
 }{
 	{
-		"C:\\\\hello\\test\\test.log",      // Path are always in windows format
-		[]string{"C:\\\\hello/test/*.log"}, // Globs can also be with forward slashes
+		`C:\\hello\test\test.log`,
+		[]string{`C:\\hello/test/*.log`},
 		nil,
 		true,
 	},
 	{
-		"C:\\\\hello\\test\\test.log",       // Path are always in windows format
-		[]string{"C:\\\\hello\\test/*.log"}, // Globs can also be mixed
+		`C:\\hello\test\test.log`,
+		[]string{`C:\\hello\test/*.log`},
+		nil,
+		true,
+	},
+	{
+		`C:\\hello\test\test.log`,
+		[]string{`C://hello/test/*.log`},
+		nil,
+		true,
+	},
+	{
+		`C:\\hello\test\test.log`,
+		[]string{`C://hello//test//*.log`},
+		nil,
+		true,
+	},
+	{
+		`C://hello/test/test.log`,
+		[]string{`C:\\hello\test\*.log`},
+		nil,
+		true,
+	},
+	{
+		`C://hello/test/test.log`,
+		[]string{`C:/hello/test/*.log`},
 		nil,
 		true,
 	},