I would like to nominate Vortex86DX to this competition.
The 800 MHz Vortex86 DX2 was released in 2009. Its performance is however WORSE than the performance of a Cyrix 6x86MX at 250 MHz.
The Vortex86DX2 eats less than 1 watts, and it is a 11 year old cpu, so of course, nowdays it is hard to put it into perspective.
HOWEVER, it was released 16 years after the Pentium1, it has 256 kbyte L2 cache, DDR2 memory controller, and the processors clock speed is 800 mhz.
Yet, its unable to beat the Pentium1 or the Cyrix 6x86MX (these dont even have l2 cache whatsoever).
When bench testing the FPU of the Vortex86DX, it's only giving 33 megaflops, either the fpu works on a separate 33 mhz clock, or either the fpu is fully implemented from microcode, without any support at hardware level.
In theory, the ALU has two pipelines, its in-order superscalar design, however the pentium1 and cyrix 6x86mx is also in-order superscalar, so probably they have messed up something very very badly in the vortex86dx.
The Vortex86 family is based off on rise mp6, but the performance of the Vortex86DX is very far from the mp6 clock-to-clock.
When running my game engine, the Cyrix 6x86MX performs 5.9 fps, and the Vortex86DX performs at 5.9 fps. (Again, the Cyrix 6x86MX runs at 250 MHz, and the Vortex86DX runs at 800 mhz).
Its not just my game engine which is slow (which also uses floating point in its vertex processor). Even loading the linux kernel itself is quite of slow, decompressing the linux kernel is about two times slower than on the Cyrix machine.
Its very hard to find any test where the Vortex86DX outperforms the Cyrix6x86MX.
By the way, the Vortex86MX is a totally nice CPU, they have fixed this performance issue (thats about 2x-3x faster on the same clock speeds than the Vortex86DX).