This was very tough indeed.   I found the NW quadrant absolutely fiendish, but got there in the end.   Solving time, 67 minutes.    As in previous puzzles by Tees, this draws on very wide and sometimes unusual cultural references.

* = anagram  < = reversed

ACROSS

1 Robert P(IRS)IG      My last answer.   IRS = Internal Revenue Service (US)

5 HYPE RION   noir<     Poem by Keats

9 P (EER GYN) T    (energy)* in PT   Play by Ibsen

10 T(W)ENT Y    w = women   y = close to boundary (last letter)

11 BUM PP O    Character from the Deerslayer by James Fenimore Cooper

12 PENTAGON   Double definition

14 PRIORITISING   (Origin spirit)*

17 EVANGELISTIC   (gives a client)*

20 SISYPHUS   From Greek mythology

22 EVA (Braun) DER (the in German)

23 Eugene O’NEILL    one ill

25 AT HEISTS

26 PRESCOTT   (protects)*

27 MANS(i)ON    criminal family from 1960s in US.

DOWN

2 I REFU(e)L     last note spent  = take away the last letter which is also one of the musical notes A to G, I think.

3 SCRAPE PENNY    Little girl = abbreviated name.    Archaic word so ‘once’.

4/13 GAY POLICE ASSOCIATION   Cryptic definition

6 PUT IN

7 RYE    Hidden, indicated by ’sandwiches’  A gypsy gentleman

8 OUTPOINT   (tit pun oo)*   pair = two ducks i.e. no runs scored in either innings from cricket, I think

15/5D  TOTTENHAM HOTSPUR     (at Portsmouth then)*

16 TV DINNER   Pun on ’set’

18 INSTANT    Close to a straight definition

19 GEN (TO)O     TO = telegraph office    Geno Washington (musician)

21 (Ot)HELLO     Liked this    OT = overtime

24 IBS(en)     unmeasured = take away en = measure (printing).   It’s an abbreviation - Irritable bowel syndrome

I have to say I found this a boring puzzle with some clues so obvious that I yawned.  6d made me think for
a while, and 13a held me up until I remembered that setters do love cricket!
ACROSS

1.    OLDEST - ( *led-to- s)
4.    CONFUSED -(dd)
9.    PISTOL -(hidden in  chaP-IS-TOLd)
10.  INJURIES  -(in -juries)
11.  SHRUBS  - (*s-bush -r)
12.  SNIFFING -(s-niff-ing - ‘to sing’ as in ‘inform’)
13.  LEG - ( dd - ‘leg’  of a race, and cricket position)
14.  TICKLE  - (*lick- toe without ‘o’)
17.  LANTERN - (*l tanner)
21.  MEDIUM - ( dd)
25.  TOE -( t- one without ‘n’)
26.  CHAMPION - ( c-h-ampion - campion, white or red, wild flower of hedgerows .)
27.  SKETCH - (s-ketch)
28.  ORIGINAL -(dd)
29.  PAINTS - (pa-i-nts)
30.  SKELETON - (skeleton - universal key and ’skeleton in the cupboard’, phrase denoting
                                  a family’s shameful secret)
31.  DEPTHS  - ( pt in *shed)

DOWN

1.    OPPOSITE - (*soot pipe)
2.    DISTRICT  - ( di-strict - belt as in ‘commuter belt, green belt etc.)
3.    SNOWBALL - (dd.  term for various puddings, mainly made of meringue, but sometimes more
                                   like egg custard.)
5.    OWNING -(hidden in thr-OWN-IN-G-aol)
6.    FLUFFY - (fluff-y-  two slang terms for the desirable female - crumpet, or a piece of fluff)

7.    SPIRIT - (dd)
8.    DESIGN - (*dines-g)
12.  SECTION - (dd. - to section someone is to put him or her into a mental hospital)
15.  EAR -(  hidden in h-EAR-d)
16.  ARM - what can I say?
18.  NECKLACE - ( ditto)
19.  DISTINCT  - (di-*sint-ct)
20.  EMPHASIS - ( *shame about p - i-s)
22.  ACROSS - (a-cross)
23.  MARINE - (* in armed without ‘d’)
24.  UPSIDE -( up-side)
25.  TOMATO - (tom- at(E)-o  - as someone said recently, a fruit not a veg. but do not serve with custard!)

I found this on the easy side - solving time, 11 mins.

* = anagram  < = reversed

ACROSS

1 WOLF RAM

5 C (HIS) EL(l)   his = the man’s   prison room = cell

10 SETT(L)ER   L = 50 in Roman numerals

11 A P (PO) INT      A two-letter river, well-known to solvers

12 LIS(Z)T   Variable (from algebra) can be x, y, or (as here) z

13 I’M PARTING

14 OBSOLESCENT    (Celeb’s not so)*

18 TRA(i)NS FORMER

21 APPETISER   (Peter’s pie)*

23 NAIRA     Hidden reversal - basic currency unit of Nigeria

24 INRO ADS

25 IRON OUT   Golf club = iron.     In normal golf round of 18 holes, the first 9 are known as ‘out’

26 REA SEA   cf seared

27 DATA SET   A (article) in (stated)*

DOWN

1 WI(SE)LY

2 LU (TI) ST    it<

3 R ELATION S    parson’s heart = RS (middle letters)

4 MARTIN SCORSESE   (minor actresses)*

6 HYPER     Cleverly hidden

7 SPIRITED   (priest I’d)*

8 LIT I GATE    lit = vandalised, I think.     Not sure if they are exactly equivalent

9 HAPPILY MARRIED   Not a dict phrase, I think, but very familiar.   Cryptic definition

15 SP (RING) OUT

16 S (second) TEAM (side) I (one) ER (first letters)

17 H (A MP) E RED

19 MINORS   “Miners”

20 PA’S T IT

22 T (first letter of threaten) RACE

dd = double definition
cd = cryptic definition
rev = reversed or reversal
ins = insertion
cha = charade
ha = hidden answer
*(fodder) = anagram

Another delightful assigment as I get to blog Paul, who is never boring nor easy, although I must say, this one was not as difficult as his normal.

Across
1 COINCIDE Cha of coin ( a penny perhaps) Cide (sounds like side or team)
5 APOLLO A poll (vote) o (zero) Sun god per Greek mythology
9 OVATIONS Cha of OVA (eggs) TIONS *(sit on) The standing and the sitting made this clue that much out of the ordinary
12 SECRETARIES Another clue that makes Paul such an amusing compiler. Secret + Aries (zodiac sign)
15 ACRID Ins of R in ACID (tart)
17 POOL TABLE Pool (mere) Table (list) The cha may be mundane but the definition was superb … one’s pocketed and Paul carried on using this “one’s …” device for other clues as well
18 COCKROACH Simple cha cock (lift, see Chambers cock1vt)
19 EXTRA A very misleading dd

20 DOUBLED BACK Doubled (huge cups?) back (champion) Somehow I think this clue is a tad flawed … doubled is either a verb or an adjective. If the solution had been “doubles back” then “returned” would be incompatible … my only misgiving about this puzzle. Addendum :Thanks to ACP, I am now wiser to the fact that Paul was referring to Double D bra size (huge cups). I must still be dreaming about Pamela Anderson, who I often see without cups :-)

24 ENDIVE There is a typo in the on-line version Kll should be Kill
Cha of End (kill) I’ve (Paul’s)
25 DAZZLING dd
26 LIABLE (p) liable / subject to capital gains tax
27 HYPNOSIS Short simple and sweet cd

Down
1 CROSSPATCH The “one’s …” device mentioned in 17A is used with great effect here
2 INACCURACY Another very good “one’s …” clue - curacy being a clergyman’s office
3 CHILE play on Chile, the country sounding the same as chilly which the Sahara Desert certainly isn’t (except maybe at night)
4 DENTAL PLAGUE Ins of *(ten) in DAL (rev lad) + plaque (tablet)
6 PRAISE THE LORD *(Tory leadership minus Y)
8 ODDS Ins of DD (Doctor of Divinity or theologian) in OS (outsize or fat)
11 TIMOTHY LEARY Ins of I’M O (setter’s love) THY (solver’s) L (left) in TEARY (sad) for Timothy Francis Leary (1920–1996), an American writer, psychologist, futurist, and advocate of psychedelic drug research and use
13 OBITUARIES An excellent cd and it even sounds like the last rites :-)
14 REPACKAGES *(cake grapes)
16 DAREDEVIL Ins of RE (about) in DAD (parent) Evil (immorality)
21 DOZEN I simply love this cha of doze (sleep) N (noon)
22,10 REAL MADRID real mad (how an American would say if he’s very angry) rid (deliver)
23 IDEA I DEA (d) Remember those old cartoon where a light bulb over one’s head meant a brilliant brainwave or idea

Here’s a Cinephile puzzle with a non-cryptic theme - synonyms of “crazy”. While it has a few fine clues (I like 12A, 14A and 27A), it also has a one that I do not understand (16D) and two that I think are rather poor (17A and 27D).

Across
9. ULTRAHIGH - anagram of HUGH TRIAL
10. PLATO - homophone + TO
11. KNEIDEL - ID (I had) in KNEE (joint) + L (plate)
12 METHANE - “me thane”
12, 18, 23, 26: OLD BOY NETWORK - BOYNE (battle) + TWO (two) in anagram of LORD + K (king)
14. NUTCRACKERS - NUT (crazy fellow) + CRACKERS (crazy)
17. SHEET - SHE (female) + ET (cosmonaut)
19. UNLIT - “a bed” in French
21. BANANA SPLIT - BANANAS (crazy) + L (student) in PIT (mine)
25. TURF WAR - cryptic definition
27. TROLLEY - “off one’s trolley”
28. GONER - G (good) + ONE (one) + [yea]R
29. KINGS PAWN - KIN (family) + SPAWN (young produced on a string)

Down
1, 6. CUCKOO SPIT - CUCKOO (crazy) + S[peculator] + PIT (mine)
2. ATTENDEE - A (a) + TEN (ten) + D (old pence) in TEE (letter say)
3. PADDINGTON - cryptic definition (”a ton of padding” is a heavy makeweight)
4. BILL - double definition
5. RHYME ROYAL - anagram of TRULY MERRY
7. DAMAGE - DAM (mother) + AGE (how old she is)
8. SOMERSET - SOME (few) + anagram of REST
15. TUBE STRIKE - U (turn) + BEST (ideally) in TRIKE (three-wheeler)
16. COURTHOUSE - ???. Another one where I fail to grasp the word play.
17. SABOTAGE - A (a) + BOT (larva) in SAGE (herb)
20. LONGLEAT - LONG (extended) + LEAT (millrace)
22. NERINE - hidden word
24. TRYING - double definition
27. TANK - cryptic definition. But a tank does not exactly contain caterpillars; it has caterpillar treads on it.