A medication delivery and monitoring system and methods whereby drugs are safely delivered to a patient, monitored in real-time during delivery and crucial events are recorded during delivery to provide real-time, on-line information and detail for an audit trail. A novel safety label cradle unit is disclosed. Safety label cradles (SLC's) are provided in a plurality of sizes to match varying sizes of syringes which are disposed on a cradle of the SLC to provide a constant needle height on the SLC unit independent of syringe volume (barrel diameter). A selected SLC is securely affixed to a syringe by an adhesively backed label wrapping. The label is preprinted to provide drug identification indicia and drug preparation information. The information is automatically read into the system from the label. A novel delivery station of the system monitors drug delivery as a plunger of the syringe is pushed to deliver a drug to a patient. A smart tray in cooperation with a slider portion of the SLC is used to selectively deliver drugs to a port in the IV set. The smart tray comprises a first portion for carrying SLC units, an attachable second portion having a control panel for operating the system and a cover for lockably affixing the SLC units to the tray.