Looking through the Bulbapedia learnset entries for each HM move, I have found no instances within each HM set where a Pokemon learn it, but its evolution can not;
- Cut (HM01)
- Fly (HM02)*
- Surf (HM03)*
- Strength (HM04)
- Flash (HM05 Gen 1-3)
- Venonat/Venomoth can to learn Flash in Yellow, but not in R/B. Venonat loses the ability to learn flash in Gen 2
- Hoothoot/Noctowl lose the ability to learn Flash in Gen 4, although it's no longer an HM.
- Defog (HM05 D/P/Pt)
- Whirlpool (HM05 Hg/Ss - HM06 Gen 2)
- Waterfall (HM05 Gen 5 - HM07 Gen 2-4)
- Rock Smash (HM06 Gen 3-4)
- Dive (HM06 Gen 5 - HM08 Gen 3)
- Rock Climb (HM08 Gen 4)
There are a few fringe cases that pop up in earlier generations (Mostly between Red Blue and Yellow) where a Pokemon might learn the HM in one game and then be traded to another where its evolution cannot. There may also be unmentioned cases of this between Gens 1 and 2, however the Time Capsule was fairly restrictive in what could be sent back.
*Pikachu is an interesting side case - As there are event and side-game transfers that can give you a Pikachu with Fly, or even Surf (there's also a surfing Pichu). However in none of these instances can Pikachu be taught the moves from an HM.
I had a play with a damage calculator I found online and my conclusion is: there are way too many variables to produce a definitive answer: base stats, IVs and Nature all play a part, even at level 5.
If your Pokemon has perfect IVs and beneficial Nature and your opponent has 0 IVs and negative Nature, it looks like you could deal at least an extra 20% damage than if those stats were reversed. I tried a good Snivy against a bad Tepig and got 42% damage from using Tackle, whereas a bad Oshawott against a good Snivy only did 14% damage with Tackle.
In my experience, using any status move is not worthwhile. It always takes the same number of moves before your opponent is KO'd. Example: assume an average damage of 20%, that would normally take 5 Tackles to KO your opponent. If you used Leer first, Tackle would deal ~30% damage (20*1.5). Now it takes Leer + 4 Tackles, so you don't gain anything.
Also note that your opponent uses moves randomly, which you can benefit from: Tackle>Leer>Tackle always does less total damage than Leer>Tackle>Tackle.
My advice: never use more than one status move, and if you do use one always use it as the first move. Then just spam Tackle.
Best Answer
While an event Pokémon technically could come with EVs, I don't think any ever have.
Since you specified level 100, it sounds like you're concerned about them not being able to gain any EVs. If my hunch is correct, you don't need to worry about that in Gen V (their effort values are applied independently from experience). For older gens, you can check out the Box Trick (and read that anyway if you're interested; there's a note at the bottom about how it works in Gen V).