Short answer: both are discontinued, so this only matters if you are buying used. Used, the Sennheiser HD 558 is the better pick: it ranks #87 of 523 over-ear headphones by sound quality (rated 4.2/5), against #258 (rated 3.6/5) for the Sennheiser HD 555. If you want one new, the Sennheiser HD 550 ranks #8 at $199.95.

What the Sennheiser HD 555 does well: Measured response gives it a solid Harman preference score of 73 with a 3.22 dB spread, and its mids sit within about 0.5 dB of target, so vocals and instruments sound natural. The tradeoff: Discontinued, so it is mainly found used.
The Sennheiser HD 558 is the better-sounding choice. An open back over-ear with a high preference score of 86 and a light 0.6 lbs (260 g) frame. The catch: Sub bass rolls off early, falling 6 dB below target at 38 Hz, a 5.2 dB peak near 3.1 kHz adds glare, and dips near 10 kHz and 11.5 kHz dull the top treble.
Buy the Sennheiser HD 558 only if you find one used in good condition; both are discontinued, and it is the better rated of the two. For a new speaker, start with the Sennheiser HD 550 instead.
Still deciding? The full Headphones rankings cover every ranked option.
Measured response gives it a solid Harman preference score of 73 with a 3.22 dB spread, and its mids sit within about 0.5 dB of target, so vocals and instruments sound natural.
eBayAn open back over-ear with a high preference score of 86 and a light 260 g frame.
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Specifications Side By Side
| Sennheiser HD 555 | Sennheiser HD 558 | |
|---|---|---|
| Price | $169.95 Discontinued | $179.99 Discontinued |
| Ranked | #258 of 523 in Over-Ear Headphones | #87 of 523 in Over-Ear Headphones |
| Form Factor | Over-ear | Over-ear |
| Back | Open | Open |
| Connection | Wired | Wired |
| Driver Type | Dynamic | Dynamic |
| Impedance | 50 ohms | 50 ohms |
| Sensitivity | 112 dB/V | 112 dB |
| Frequency Response | 15Hz - 28kHz | 15Hz - 28kHz (Manufacturer specified) |
| Weight | 0.6 lbs (260 g) | 0.6 lbs (260 g) |
| Harman Preference Score | 73 (measured by oratory1990, via AutoEQ) | 86 (1 squig.link measurement, calibrated to AutoEQ) |
| Deviation From Target | 3.22 dB standard deviation | 2.38 dB standard deviation |
| Tonal Tilt | +0.08 (negative is warmer, positive brighter) | -0.04 (negative is warmer, positive brighter) |
| Sub-bass Extension | Falls 6 dB below target at 75 Hz (-10.7 dB at 30 Hz) | Falls 6 dB below target at 38 Hz (-8.8 dB at 30 Hz) |
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