The problem your having with your shoulder is more than likely that you are or have gone to deep and caused a stretching of the anterior joint capsule (often do to full ROM benching, dumbell benching below the pectoral line, dips beyond a 90 deg. elbow angle and leaning back during front lat pulldowns - upright rows & traditional lateral raises can also screw up the area too!)
First you need to have YOUR end range of motion determined for benching, for many the bar touching the chest is too deep and every rep done like that causes shoulder damage - When you lie on a bench or retract your scapula at the START of a pulldown you decrease motion of the scapula, disrupting scapula-humeral rhythm and placing increased stress on the glenohumeral joint, the excess ROM also stretches out the anterior capsule leading to anterior shoulder instability - so what you probably have done is overstretched the anterior capsule allowing the humerus to move around an irritate other tissues. When you do your full ROM dips you are literally shoving the humerus up into the acromion and irritating all the tissue in between - can lead to bursitits, tendonitis, R. cuff problems and impingement syndromes.
I would get it evaluated. I would also change my routine and add in rotator cuff strecthing & strengthing, scapular retraction & depression, lay off dips and eventually go back with a reduced ROM, stop flat benching - move to DB's on the floor and then a stability ball and then back to the bench. Make sure my pulldowns / pullups are 100% vertical and use an underhand or neutral grip, avoid upright rows and swtich lateral raises to the L-lateral raise and avoid the standing calf raise machine - the lever arms can cause compression injuries or aggrevate other problems in the shoulders.
To help with scapula movement and control and rehab - great series of vids by Ian King:
roduct ID: KSIV4 Category: Videos
Injury Prevention and Rehabilitation Video Series
Description: This video program is a live shoot from a two-day seminar series that focuses exclusively on injury prevention and rehabilitation. This video Ian will share with you Ian's unique and highly effective methods for preventing & rehabilitating injuries.
Product ID: GBV1 Category: Videos
Ian Kings Guide to Control Drills Video
Description: This tape contains one of Ian’s best-kept secrets – methods he has developed but doesn’t speak about too much. One of the reasons is that they are complex to teach, best suited to a visual demonstration – and this is what you get with this video!
http://www.kingsports.net/
Good LucK!