2D organic crystals exhibit efficient charge transport and field‐effect characteristics, making them promising candidates for high‐performance nanoelectronics. However, the strong Fermi level pinning (FLP) effect and large Schottky barrier between organic semiconductors and metals largely limit device performance. Herein, by carrying out temperature‐dependent transport and Kelvin probe force microscopy measurements, it is demonstrated that the introducing of 2D metallic 1T‐TaSe2 with matched band‐alignment as electrodes for F16CuPc nanoflake filed‐effect transistors leads to enhanced field‐effect characteristics, especially lowered Schottky barrier height and contact resistance at the contact and highly efficient charge transport within the channel, which are attributed to the significantly suppressed FLP effect and appropriate band alignment at the nonbonding van der Waals (vdW) hetero‐interface. Moreover, by taking advantage of the improved contact behavior with 1T‐TaSe2 contact, the optoelectronic performance of F16CuPc nanoflake‐based phototransistor is drastically improved, with a maximum photoresponsivity of 387 A W−1 and detectivity of 3.7 × 1014 Jones at quite a low Vds of 1 V, which is more competitive than those of the reported organic photodetectors and phototransistors. The work provides an avenue to improve the electrical and optoelectronic properties of 2D organic devices by introducing 2D metals with appropriate work function for vdW contacts. A new approach is reported for contact engineering of 2D F16CuPc nanoflakes by using vdW contacts with 2D metal, 1T‐TaSe2. It is demonstrated that their efficient charge injection reduces Schottky barrier height and contact resistance, but results in superior charge transport, which further enables the significant enhancement of optoelectronic performance.