I've decided to go through all previous level design contests and LOTY contests and list the winners and 2nd placements.
3rd placements were often not documented or if they were are often a result of ties between two winners. LOTY often did document those though.
In a few cases persons also occupied also multiple placements - like levels from person A took 2nd and 3rd place.
I plan to update the list after future contests. Enjoy! Official level design contests 1st 2nd 3rd#1 Crane IchoTolot (Lemmini)
#2 Nepster WaffLem
#3 WaffLem/IchoTolot IchoTolot/Möbius
#4 IchoTolot Nepster (Lix)
#5 Crane IchoTolot
#6 Geoffster Crane
#7 GigaLem IchoTolot
#8 DRAW/CANCELED (IchoTolot/Nepster) - As no one really voted!
#9 Flopsy Apjjm
#10 BulletRide Apjjm
#11 zanzindorf Crane
#12 Colorful Arty Namida
#13 Nessy IchoTolot
#14 Nessy Raymanni
#15 Colorful Arty SQron188
#16 Nessy Crane
#17 Crane Nessy
#18 Namida Crane
#19 Flopsy+IchoTolot (Tie) - Armani
#20 DireKrow Armani
#21 IchoTolot Armani
#22 Armani Nessy
#23 Kingshadow3 Armani
#24 IchoTolot+tan x dx (Tie) - Kingshadow3
#25 Armani IchoTolot
#26 NieSch Armani
#27 Simon (Lix) - NieSch
#28 Kingshadow3 Armani Simon (Lix)
#29 Armani kaywhyn IchoTolot
Overall count of 1st placements: 5: IchoTolot
3: Armani, Crane, Nessy
2: Colorful Arty, Flopsy, Kingshadow3
1: BulletRide, DireKrow, Geoffster, GigaLem, Namida, Nepster, NieSch,Simon, tan x dx, WaffLem, zanzindorf
Overall count of 2nd placements:6: IchoTolot
5: Armani
4: Crane
2: Apjjm, Nessy
1: kaywhyn, Namida, Nepster, Möbius, Raymanni, SQron188, WaffLem
Overall count of 3rd placements (in case of tied 1st place, or 2 levels of the same author reaching 1st and 2nd place):1: Armani, IchoTolot, Kingshadow3, NieSch, Simon
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Official level of the year contests 1st 2nd 3rd2015 IchoTolot GigaLem Geoffster
2016 Nepster Gronkling
2017 Flopsy
2018 tan x dx Namida kieranmillar
2019 IchoTolot+Namida (Tie) - Crane
2020 DireKrow Armani IchoTolot
2021 Nessy IchoTolot
2022 Armani+IchoTolot (Tie) - IchoTolot
Overall count of 1st placements: 3: IchoTolot
1: Armani, DireKrow, Flopsy, Namida, Nepster, Nessy, tan x dx
Overall count of 2nd placements (if present):1: Armani, GigaLem, Gronkling, IchoTolot, Namida
Overall count of 3rd placements (if present):2: IchoTolot
1: Crane, Geoffster, kieranmillar