I had pretty much the exact same PR's as you 3 years ago and did the same mistake as you, figured I could run 14:50's based on equivalent calculators and faded.
I don't think your training is the problem, but realistically if you've run 8:33 you're in 15:00-15:10 shape, next race I would try going out in 9:00-9:05 thru 3k.
I also think that 5k's on the track are a lot harder than 3k's mentally. When I was starting to run 5k's on the track I went in expecting to feel controlled through 3k and having to push the last 2k, but I've found that in my best, even split races it felt like I was hanging on from 2k in. Having competition and/or pacers helps a lot with this.