diff --git a/base/constants.jl b/base/constants.jl
index 34727f23e60a8f..d3e3ddc7e68eae 100644
--- a/base/constants.jl
+++ b/base/constants.jl
@@ -21,6 +21,37 @@ end
 =={s}(::MathConst{s}, ::MathConst{s}) = true
 ==(::MathConst, ::MathConst) = false
 
+# MathConsts are irrational, so unequal to everything else
+==(x::MathConst, y::Real) = false
+==(x::Real, y::MathConst) = false
+
+# MathConst vs FloatingPoint
+<{T<:FloatingPoint}(x::MathConst, y::T) = T(x,RoundUp) <= y
+<{T<:FloatingPoint}(x::T, y::MathConst) = x <= T(y,RoundDown)
+
+<=(x::MathConst,y::FloatingPoint) = x < y
+<=(x::FloatingPoint,y::MathConst) = x < y
+
+# MathConst vs Rational
+stagedfunction <{T}(x::MathConst, y::Rational{T})
+    bx = big(x())
+    bx < 0 && T <: Unsigned && return true
+    rx = rationalize(T,bx,tol=0)
+    rx < bx ? :($rx < y) : :($rx <= y)
+end
+stagedfunction <{T}(x::Rational{T}, y::MathConst)
+    by = big(y())
+    by < 0 && T <: Unsigned && return false
+    ry = rationalize(T,by,tol=0)
+    ry < by ? :(x <= $ry) : :(x < $ry)
+end
+<(x::MathConst, y::Rational{BigInt}) = big(x) < y
+<(x::Rational{BigInt}, y::MathConst) = x < big(y)
+
+<=(x::MathConst,y::Rational) = x < y
+<=(x::Rational,y::MathConst) = x < y
+
+
 hash(x::MathConst, h::UInt) = hash(object_id(x), h)
 
 -(x::MathConst) = -float64(x)
diff --git a/test/numbers.jl b/test/numbers.jl
index f2210642896ecf..b876c2622b1968 100644
--- a/test/numbers.jl
+++ b/test/numbers.jl
@@ -814,6 +814,19 @@ end
 @test !(1//3 == NaN)
 @test !(1//3 > NaN)
 
+@test Float64(pi,RoundDown) < pi
+@test Float64(pi,RoundUp) > pi
+@test !(Float64(pi,RoundDown) > pi)
+@test !(Float64(pi,RoundUp) < pi)
+@test Float64(pi,RoundDown) <= pi
+@test Float64(pi,RoundUp) >= pi
+@test Float64(pi,RoundDown) != pi
+@test Float64(pi,RoundUp) != pi
+
+@test 2646693125139304345//842468587426513207 < pi
+@test !(2646693125139304345//842468587426513207 > pi)
+@test 2646693125139304345//842468587426513207 != pi
+
 @test sqrt(2) == 1.4142135623730951
 
 @test 1+1.5 == 2.5