Hi Bagheera33,
5a definition is "not smiley" - 3 letter synonym for "one" after S(py) + 2 letters for "bill" + F(oot)
23a definition is "bore" - 6 letter synonym for "equipped" around R(iver)
2d definition is "telethon" (as an example) - 7 letter place name of where Ipswich Town play + anagram of "water + duo"
13d definition is "instrument" - 4 letter synonym for "old woman" inside 3 letter synonym for "evil" and 2 letters for "times" (think multiplication)