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I've sneaked under 20 at Dulwich (flat). I'd like to be honest.
I ran my first sub 20min 5k yesterday, along the river between Greenwich and Woolwich. I felt I could have gone a bit faster without the thames path's ramps and chicanes etc. Could do it on a track. Could do it indoors with no wind. Could do it in a vacuum in perfectly straight line.
Then I ran up the hill in Greenwich Park in the dark and across Blackheath and remembered why running is actually fun :)
Downhills definitely
Speaking from my recent xc races. Everyone goes up at a similar speed, if you can let gravity take over and just get your feet turning over quickly, you can really gain on the downhills.
Better yet, go somewhere flat