sh is first seen in Old English when appearing in words such as ‘fish’; however the earliest words used the sound but used the spelling ‘fc’ more often until Middle English.
kn also appears in Old English but the pronunciation was rather different, indeed ‘knee’ and ‘knife’ were pronounced ‘ker-nee’ and ‘ker-nife’ until the 17th century and hung on regionally after that.
ch makes its first appearance in Latin and Greek around the 2nd century, slowly influencing English pronunciation over several centuries.
ph is recorded in Greek centuries before Old English ever came into existence, the use in English coming in slowly and almost with individual words.
wr appears in English for the first time in the 9th century. Originally the ‘w’ element was pronounced, but disappeared by the 16th century.
ck is first seen in the Dark Ages, when Old English and Old Scandinavian words of similar spelling united.
ss is seen for the first time in a manuscript featuring a poem by Wolfdietrch around the end of the 13th century.
ea is seen in English from the early 16th century.
oa is seen from the earliest times of the development of Old English.
ee is also found from the earliest examples of Old English.
oo appears rather late in the development of Modern English, seen for the first time in Middle English around the 16th century.
ai is found from around the later years of Old English, prior to this ‘ay’ was more common.
au is seen from the late Old English era, but even today as different vowel sounds – as seen in ‘laugh’ and ‘taut’.
ow is also seen in two different forms, as in blow and owl, both found from the late Old English period.
ou makes its debut in the early Middle English period.
There are also examples of trigraphs – tch, igh, ear, eer, dge, ere – all of which are mere extensions and therefore rather later developments.
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