You have to add the size of the legend box to the ylim range
#Plot an empty graph and legend to get the size of the legend
x <-1:10
y <-11:20
plot(x,y,type="n", xaxt="n", yaxt="n")
my.legend.size <-legend("topright",c("Series1","Series2","Series3"),plot = FALSE)
#custom ylim. Add the height of legend to upper bound of the range
my.range <- range(y)
my.range[2] <- 1.04*(my.range[2]+my.legend.size$rect$h)
#draw the plot with custom ylim
plot(x,y,ylim=my.range, type="l")
my.legend.size <-legend("topright",c("Series1","Series2","Series3"))