diff --git a/src/libraries/Common/tests/TestUtilities/System/PlatformDetection.Windows.cs b/src/libraries/Common/tests/TestUtilities/System/PlatformDetection.Windows.cs
index 6448f7cc42d4b1..a06d545cd1c72b 100644
--- a/src/libraries/Common/tests/TestUtilities/System/PlatformDetection.Windows.cs
+++ b/src/libraries/Common/tests/TestUtilities/System/PlatformDetection.Windows.cs
@@ -24,6 +24,7 @@ public static partial class PlatformDetection
         public static bool IsWindows8x => IsWindows && GetWindowsVersion() == 6 && (GetWindowsMinorVersion() == 2 || GetWindowsMinorVersion() == 3);
         public static bool IsWindows8xOrLater => IsWindowsVersionOrLater(6, 2);
         public static bool IsWindows10OrLater => IsWindowsVersionOrLater(10, 0);
+        public static bool IsWindowsServer2019 => IsWindows && IsNotWindowsNanoServer && GetWindowsVersion() == 10 && GetWindowsMinorVersion() == 0 && GetWindowsBuildVersion() == 17763;
         public static bool IsWindowsNanoServer => IsWindows && (IsNotWindowsIoTCore && GetWindowsInstallationType().Equals("Nano Server", StringComparison.OrdinalIgnoreCase));
         public static bool IsWindowsServerCore => IsWindows && GetWindowsInstallationType().Equals("Server Core", StringComparison.OrdinalIgnoreCase);
         public static int WindowsVersion => IsWindows ? (int)GetWindowsVersion() : -1;
@@ -173,6 +174,7 @@ internal static Version GetWindowsVersionObject()
 
         internal static uint GetWindowsVersion() => (uint)GetWindowsVersionObject().Major;
         internal static uint GetWindowsMinorVersion() => (uint)GetWindowsVersionObject().Minor;
+        internal static uint GetWindowsBuildVersion() => (uint)GetWindowsVersionObject().Build;
 
         internal static bool IsWindowsVersionOrLater(int major, int minor, int build = -1)
         {
diff --git a/src/libraries/System.Globalization/tests/IcuTests.cs b/src/libraries/System.Globalization/tests/IcuTests.cs
index 671c5036fbd979..0990c710f6d63b 100644
--- a/src/libraries/System.Globalization/tests/IcuTests.cs
+++ b/src/libraries/System.Globalization/tests/IcuTests.cs
@@ -10,7 +10,7 @@ namespace System.Globalization.Tests
     public class IcuTests
     {
         private static bool IsIcuCompatiblePlatform => PlatformDetection.IsNotWindows ||
-                                                       (PlatformDetection.IsWindows10Version1903OrGreater &&
+                                                       ((PlatformDetection.IsWindowsServer2019 || PlatformDetection.IsWindows10Version1903OrGreater) &&
                                                         // Server core doesn't have icu.dll on SysWOW64
                                                         !(PlatformDetection.IsWindowsServerCore && PlatformDetection.IsX86Process));
 
diff --git a/src/native/libs/System.Globalization.Native/pal_icushim.c b/src/native/libs/System.Globalization.Native/pal_icushim.c
index 9f8994394e4afd..d23499c80b1ee1 100644
--- a/src/native/libs/System.Globalization.Native/pal_icushim.c
+++ b/src/native/libs/System.Globalization.Native/pal_icushim.c
@@ -100,6 +100,17 @@ static int FindICULibs()
     libicuuc = LoadLibraryExW(L"icu.dll", NULL, LOAD_LIBRARY_SEARCH_SYSTEM32);
     if (libicuuc == NULL)
     {
+        // On Windows Server 2019, the ICU library is installed as icuuc.dll and icuin.dll. Try to load these.
+        libicuuc = LoadLibraryExW(L"icuuc.dll", NULL, LOAD_LIBRARY_SEARCH_SYSTEM32);
+        if (libicuuc != NULL)
+        {
+            libicui18n = LoadLibraryExW(L"icuin.dll", NULL, LOAD_LIBRARY_SEARCH_SYSTEM32);
+            if (libicui18n != NULL)
+            {
+                return true;
+            }
+        }
+
         return false;
     }