“Winningest” presents an interesting problem in language change, as Bruce suggests.  The pattern in English of /Ng/ vs. /N/ alternation, where /N/ represents the velar nasal sound in “sing,” lays out roughly as below:

 

Morpheme-internally English has /Ng/, as in “finger,” “dangle,” or “Tonga.”

Before a vowel-initial inflectional suffix, English has /Ng/, as in “longer,” “strongest.”

Before a vowel-initial derivational suffix, English has /N/, as in “singer,” “hanger.”

Word-finally English as /N/, as in “sing,” “long,” etc.

 

It could be argued that /Ng/ vs. /N/ represents a productive morphophonemic alternation.  “Winningest” would support this claim, since –ing is a derivational suffix and so does not have a /g/ before an inflectional suffix.  “Winninger,” whether it occurs or not, would behave the same way for the same reason.

 

In Old English there was only /Ng/ and /Nk/, no bare /N/, since /N/ was what /n/ became by assimilation to a following velar (/g,k/).  In Middle and Modern English the final /g/ was lost in the contexts given above where /N/ now occurs by itself.

 

It can thus be argued that /g/-deletion is a regular morphophonemic rule in Modern English.

 

As a side note, this /g/-deletion is distinct from what is popularly referred to as “dropping “g,” the free variation between “walking” and “walkin’.”  This variation, which actually has nothing to do with /g/-deletion and refers instead to an orthographic practice, probably arises from the merger in Middle English of Old English present participles in –end- and gerunds in –ing.  The final /g/ of /-INg/ was lost as illustrated above, since it was word final, giving the form /-IN/, as in “walking.”  The loss of the final /d/ of the –end suffix produced the form /-In/, as in “walkin’.”  The –ing/-in’ variation reflects the distinct sources of the Modern English present participle, and although our spelling makes it look like dropping of /g/, phonologically there is no /g/ to drop.  The –in’ form simply has a different historical source.

 

Herb

 

 

 

 

 

 

 

Another observation: participles loving, winning, and losing have superlatives but not comparatives: The Canandian women's ice hockey team was the winningest in the Olympics, even winninger than the Americans.

Dick

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