I feed my two dogs at the same times.
My lab was on only two meals a day, but I have just split the quantities to make four meals.
It works really well and they eat side by side quite happily.
Sometimes, Lottie will attempt to grab some of Goldies food, but we just watch carefully and move her back.
Both our dogs are very good and very fast feeders, often it's a race to see who finishes first, so we dont have to worry about one of them not getting their quota.
I'm not sure if this way of feeding is really correct for an older adult dog, but I thought it would save any feelings of jealousy.
They both eat at 7.00, 12.30, 5.30 and 10.00