Streetmachines aren't particularly fast. They're quite heavy and optimised for comfort and stability rather than aerodynamics. I can go like stink downhill on mine because I'm not utterly terrified of hitting some pothole/gravel and wiping out (it's less scary than an upright in this respect, because you don't feel that hard braking or some catastrophic failure of the front wheel will cause you to land on your face), but unless you can carry that momentum into a climb, you pay for it overall. I find I more or less break even with an upright tourer at standard 1% rolling hills, if it's flatter the recumbent has an advantage, if it's hillier, the upwrong's faster, but then you have contact points to worry about.
The Red Baron, on the other hand, is fast on the flat, climbs slightly better than the Streetmachine on account of being 5kg lighter (although stability is more of an issue), and is usually slower downhill because while it's much more aerodynamic, you can't usually take advantage of that because you're terrified of hitting some unseen (because you can't see as much of the road in front of you) hazard that the bike isn't built to cope with. It's a revelation on a nice flat bit of decent-quality road.
(ICE Sprint is much like the Streetmachine, but doesn't roll quite as well, high-speed cornering is an art, and you don't have to worry about balance on double-bastard hills.)
IME it's headwinds where they really win, but I'm mainly in it for being able to feel my hands properly after a long ride.