Given the timings of the races, Middleton and his fellow owner Mark Lowther are planning to employ a helicopter to see both horses run.
Holly Bush Henry will line up in the £75,000 Keltbray Swinley Chase at Ascot while Golan Fortune, who was last seen finishing second in a £100,000 handicap at Sandown, reverts to novice company for the Grade Two Albert Bartlett Novices' Hurdle at Haydock.
"I've just been speaking to Mark (Lowther) who owns half of them with me and I asked him where he wanted to go and he suggested we get a chopper and do both!" said Middleton.
"They are both definitely running and we don't want to miss either.
"I rode Holly Bush Henry this morning and he felt great. It's a bit competitive but he'll have a great chance, I think.
"We've gone the opposite of what we were told - we were told he wants two miles and good ground with a tongue tie, yet he seems to love heavy ground, three miles and without a tongue tie.
"He runs with his tongue hanging out so he's not going to swallow it.
"I thought Golan was a touch unlucky the other day, he was further back than he should have been but he still ran well.
"There's only a couple rated higher than him and he's in great form otherwise he wouldn't be running, the plan was to given him a break.
"Jamie Moore will ride Golan. He schooled him earlier in the season for me, but with him being in handicaps, I've been keen to claim off him. Hopefully Sean Bowen can ride Holly Bush Henry, he goes really well for him.
"I've only got four horses and one of those, Exitas, isn't in training at the moment as he hates soft ground, so to have two running in races like this is a big deal."