diff --git a/R/pkg/NAMESPACE b/R/pkg/NAMESPACE
index db8e06db18edc..e8de34d9371a0 100644
--- a/R/pkg/NAMESPACE
+++ b/R/pkg/NAMESPACE
@@ -182,7 +182,8 @@ exportMethods("arrange",
 
 exportClasses("Column")
 
-exportMethods("%in%",
+exportMethods("%<=>%",
+              "%in%",
               "abs",
               "acos",
               "add_months",
@@ -291,6 +292,7 @@ exportMethods("%in%",
               "nanvl",
               "negate",
               "next_day",
+              "not",
               "ntile",
               "otherwise",
               "over",
diff --git a/R/pkg/R/column.R b/R/pkg/R/column.R
index 539d91b0f8797..147ee4b6887b9 100644
--- a/R/pkg/R/column.R
+++ b/R/pkg/R/column.R
@@ -67,8 +67,7 @@ operators <- list(
   "+" = "plus", "-" = "minus", "*" = "multiply", "/" = "divide", "%%" = "mod",
   "==" = "equalTo", ">" = "gt", "<" = "lt", "!=" = "notEqual", "<=" = "leq", ">=" = "geq",
   # we can not override `&&` and `||`, so use `&` and `|` instead
-  "&" = "and", "|" = "or", #, "!" = "unary_$bang"
-  "^" = "pow"
+  "&" = "and", "|" = "or", "^" = "pow"
 )
 column_functions1 <- c("asc", "desc", "isNaN", "isNull", "isNotNull")
 column_functions2 <- c("like", "rlike", "getField", "getItem", "contains")
@@ -302,3 +301,55 @@ setMethod("otherwise",
             jc <- callJMethod(x@jc, "otherwise", value)
             column(jc)
           })
+
+#' \%<=>\%
+#'
+#' Equality test that is safe for null values.
+#'
+#' Can be used, unlike standard equality operator, to perform null-safe joins.
+#' Equivalent to Scala \code{Column.<=>} and \code{Column.eqNullSafe}.
+#'
+#' @param x a Column
+#' @param value a value to compare
+#' @rdname eq_null_safe
+#' @name %<=>%
+#' @aliases %<=>%,Column-method
+#' @export
+#' @examples
+#' \dontrun{
+#' df1 <- createDataFrame(data.frame(
+#'   x = c(1, NA, 3, NA), y = c(2, 6, 3, NA)
+#' ))
+#'
+#' head(select(df1, df1$x == df1$y, df1$x %<=>% df1$y))
+#'
+#' df2 <- createDataFrame(data.frame(y = c(3, NA)))
+#' count(join(df1, df2, df1$y == df2$y))
+#'
+#' count(join(df1, df2, df1$y %<=>% df2$y))
+#' }
+#' @note \%<=>\% since 2.3.0
+setMethod("%<=>%",
+          signature(x = "Column", value = "ANY"),
+          function(x, value) {
+            value <- if (class(value) == "Column") { value@jc } else { value }
+            jc <- callJMethod(x@jc, "eqNullSafe", value)
+            column(jc)
+          })
+
+#' !
+#'
+#' Inversion of boolean expression.
+#'
+#' @rdname not
+#' @name not
+#' @aliases !,Column-method
+#' @export
+#' @examples
+#' \dontrun{
+#' df <- createDataFrame(data.frame(x = c(-1, 0, 1)))
+#'
+#' head(select(df, !column("x") > 0))
+#' }
+#' @note ! since 2.3.0
+setMethod("!", signature(x = "Column"), function(x) not(x))
diff --git a/R/pkg/R/functions.R b/R/pkg/R/functions.R
index f4a34fbabe4d7..f9687d680e7a2 100644
--- a/R/pkg/R/functions.R
+++ b/R/pkg/R/functions.R
@@ -3859,3 +3859,34 @@ setMethod("posexplode_outer",
             jc <- callJStatic("org.apache.spark.sql.functions", "posexplode_outer", x@jc)
             column(jc)
           })
+
+#' not
+#'
+#' Inversion of boolean expression.
+#'
+#' \code{not} and \code{!} cannot be applied directly to numerical column.
+#' To achieve R-like truthiness column has to be casted to \code{BooleanType}.
+#'
+#' @param x Column to compute on
+#' @rdname not
+#' @name not
+#' @aliases not,Column-method
+#' @export
+#' @examples \dontrun{
+#' df <- createDataFrame(data.frame(
+#'   is_true = c(TRUE, FALSE, NA),
+#'   flag = c(1, 0,  1)
+#' ))
+#'
+#' head(select(df, not(df$is_true)))
+#'
+#' # Explicit cast is required when working with numeric column
+#' head(select(df, not(cast(df$flag, "boolean"))))
+#' }
+#' @note not since 2.3.0
+setMethod("not",
+          signature(x = "Column"),
+          function(x) {
+            jc <- callJStatic("org.apache.spark.sql.functions", "not", x@jc)
+            column(jc)
+          })
diff --git a/R/pkg/R/generics.R b/R/pkg/R/generics.R
index e510ff9a2d80f..d4e4958dc078c 100644
--- a/R/pkg/R/generics.R
+++ b/R/pkg/R/generics.R
@@ -856,6 +856,10 @@ setGeneric("otherwise", function(x, value) { standardGeneric("otherwise") })
 #' @export
 setGeneric("over", function(x, window) { standardGeneric("over") })
 
+#' @rdname eq_null_safe
+#' @export
+setGeneric("%<=>%", function(x, value) { standardGeneric("%<=>%") })
+
 ###################### WindowSpec Methods ##########################
 
 #' @rdname partitionBy
@@ -1154,6 +1158,10 @@ setGeneric("nanvl", function(y, x) { standardGeneric("nanvl") })
 #' @export
 setGeneric("negate", function(x) { standardGeneric("negate") })
 
+#' @rdname not
+#' @export
+setGeneric("not", function(x) { standardGeneric("not") })
+
 #' @rdname next_day
 #' @export
 setGeneric("next_day", function(y, x) { standardGeneric("next_day") })
diff --git a/R/pkg/inst/tests/testthat/test_context.R b/R/pkg/inst/tests/testthat/test_context.R
index c847113491113..c64fe6edcd49e 100644
--- a/R/pkg/inst/tests/testthat/test_context.R
+++ b/R/pkg/inst/tests/testthat/test_context.R
@@ -21,10 +21,10 @@ test_that("Check masked functions", {
   # Check that we are not masking any new function from base, stats, testthat unexpectedly
   # NOTE: We should avoid adding entries to *namesOfMaskedCompletely* as masked functions make it
   # hard for users to use base R functions. Please check when in doubt.
-  namesOfMaskedCompletely <- c("cov", "filter", "sample")
+  namesOfMaskedCompletely <- c("cov", "filter", "sample", "not")
   namesOfMasked <- c("describe", "cov", "filter", "lag", "na.omit", "predict", "sd", "var",
                      "colnames", "colnames<-", "intersect", "rank", "rbind", "sample", "subset",
-                     "summary", "transform", "drop", "window", "as.data.frame", "union")
+                     "summary", "transform", "drop", "window", "as.data.frame", "union", "not")
   if (as.numeric(R.version$major) >= 3 && as.numeric(R.version$minor) >= 3) {
     namesOfMasked <- c("endsWith", "startsWith", namesOfMasked)
   }
diff --git a/R/pkg/inst/tests/testthat/test_sparkSQL.R b/R/pkg/inst/tests/testthat/test_sparkSQL.R
index 1828cddffd27c..08296354ca7ed 100644
--- a/R/pkg/inst/tests/testthat/test_sparkSQL.R
+++ b/R/pkg/inst/tests/testthat/test_sparkSQL.R
@@ -1323,6 +1323,8 @@ test_that("column operators", {
   c3 <- (c + c2 - c2) * c2 %% c2
   c4 <- (c > c2) & (c2 <= c3) | (c == c2) & (c2 != c3)
   c5 <- c2 ^ c3 ^ c4
+  c6 <- c2 %<=>% c3
+  c7 <- !c6
 })
 
 test_that("column functions", {
@@ -1348,6 +1350,7 @@ test_that("column functions", {
   c19 <- spark_partition_id() + coalesce(c) + coalesce(c1, c2, c3)
   c20 <- to_timestamp(c) + to_timestamp(c, "yyyy") + to_date(c, "yyyy")
   c21 <- posexplode_outer(c) + explode_outer(c)
+  c22 <- not(c)
 
   # Test if base::is.nan() is exposed
   expect_equal(is.nan(c("a", "b")), c(FALSE, FALSE))
@@ -1488,6 +1491,13 @@ test_that("column functions", {
     lapply(
       list(list(x = 1, y = -1, z = -2), list(x = 2, y = 3,  z = 5)),
       as.environment))
+
+  df <- as.DataFrame(data.frame(is_true = c(TRUE, FALSE, NA)))
+  expect_equal(
+    collect(select(df, alias(not(df$is_true), "is_false"))),
+    data.frame(is_false = c(FALSE, TRUE, NA))
+  )
+
 })
 
 test_that("column binary mathfunctions", {
@@ -1973,6 +1983,16 @@ test_that("filter() on a DataFrame", {
   filtered6 <- where(df, df$age %in% c(19, 30))
   expect_equal(count(filtered6), 2)
 
+  # test suites for %<=>%
+  dfNa <- read.json(jsonPathNa)
+  expect_equal(count(filter(dfNa, dfNa$age %<=>% 60)), 1)
+  expect_equal(count(filter(dfNa, !(dfNa$age %<=>% 60))), 5 - 1)
+  expect_equal(count(filter(dfNa, dfNa$age %<=>% NULL)), 3)
+  expect_equal(count(filter(dfNa, !(dfNa$age %<=>% NULL))), 5 - 3)
+  # match NA from two columns
+  expect_equal(count(filter(dfNa, dfNa$age %<=>% dfNa$height)), 2)
+  expect_equal(count(filter(dfNa, !(dfNa$age %<=>% dfNa$height))), 5 - 2)
+
   # Test stats::filter is working
   #expect_true(is.ts(filter(1:100, rep(1, 3)))) # nolint
 })