diff --git a/Sources/NIO/EventLoop.swift b/Sources/NIO/EventLoop.swift
index de42274673..e3e179cc13 100644
--- a/Sources/NIO/EventLoop.swift
+++ b/Sources/NIO/EventLoop.swift
@@ -394,7 +394,7 @@ extension NIODeadline: CustomStringConvertible {
 
 extension NIODeadline {
     public static func - (lhs: NIODeadline, rhs: NIODeadline) -> TimeAmount {
-        return .nanoseconds(TimeAmount.Value(lhs.uptimeNanoseconds - rhs.uptimeNanoseconds))
+        return .nanoseconds(TimeAmount.Value(lhs.uptimeNanoseconds) - TimeAmount.Value(rhs.uptimeNanoseconds))
     }
 
     public static func + (lhs: NIODeadline, rhs: TimeAmount) -> NIODeadline {
diff --git a/Tests/NIOTests/EventLoopTest+XCTest.swift b/Tests/NIOTests/EventLoopTest+XCTest.swift
index ce29fa339a..ab4dcba16b 100644
--- a/Tests/NIOTests/EventLoopTest+XCTest.swift
+++ b/Tests/NIOTests/EventLoopTest+XCTest.swift
@@ -54,6 +54,7 @@ extension EventLoopTest {
                 ("testAndAllSucceedWithZeroFutures", testAndAllSucceedWithZeroFutures),
                 ("testCancelledScheduledTasksDoNotHoldOnToRunClosure", testCancelledScheduledTasksDoNotHoldOnToRunClosure),
                 ("testIllegalCloseOfEventLoopFails", testIllegalCloseOfEventLoopFails),
+                ("testSubtractingDeadlineFromPastAndFuturesDeadlinesWorks", testSubtractingDeadlineFromPastAndFuturesDeadlinesWorks),
            ]
    }
 }
diff --git a/Tests/NIOTests/EventLoopTest.swift b/Tests/NIOTests/EventLoopTest.swift
index 45d32a8ba8..8a53e742c9 100644
--- a/Tests/NIOTests/EventLoopTest.swift
+++ b/Tests/NIOTests/EventLoopTest.swift
@@ -795,4 +795,13 @@ public final class EventLoopTest : XCTestCase {
             }
         }
     }
+
+    func testSubtractingDeadlineFromPastAndFuturesDeadlinesWorks() {
+        let older = NIODeadline.now()
+        Thread.sleep(until: Date().addingTimeInterval(0.02))
+        let newer = NIODeadline.now()
+
+        XCTAssertLessThan(older - newer, .nanoseconds(0))
+        XCTAssertGreaterThan(newer - older, .nanoseconds(0))
+    }
 }