99 on the Button ($10NL).

I seem to have trouble with mid-pairs. Villain was 55/18/1.25 here, but only over 22 hands. He had raised from UTG with KT a few hands earlier.

What is the best way to play this hand on all streets?
I think I completely messed the bet sizing up, as Villain only has $1.82 remaining after he calls the flop raise.

iPoker No-Limit Hold'em, $0.10 BB (5 handed) - Converter Tool from FlopTurnRiver.com

Hero (Button) ($10.84)
SB ($3.25)
BB ($10)
UTG ($4.92)
MP ($10)

Preflop: Hero is Button with 9, 9
UTG raises $0.40, 1 fold, Hero calls $0.40, 2 folds

Flop: ($0.95) 2, 5, 5 (2 players)
UTG bets $0.95, Hero raises $2.70, UTG calls $1.75

Turn: ($6.35) A (2 players)
UTG checks, Hero bets $7.74 (All-In)

if villian only has that much left after that flop and he's that loose i suggest pushing him all in on the flop after he bets out....

just ship him on the flop if you want to go with the hand