As far as I know during the Iran-Iraq War in 1980s, Iran's F-14s, equipped with Phoenix missiles, capable of identifying and destroying six targets simultaneously from a range of eighty kilometers, inflicted heavy casualties on the Iraqi air force, which was forced to disperse its aircraft to Jordan and Oman. The capability of the F-14s and F-4s was enhanced by the earlier acquisition of a squadron of Boeing 707 tankers which extending their combat radius to 2,500 kilometers with in-flight refueling.
Iranian F-14 Tomcats were used like miniature AWACS reporting Iraqi fighter operations to Iranian air defense command with their powerful radars. In response, Iraqi Mirage F1-EQ fighters flew high-speed low-altitude profiles, well below the Tomcat's radar limits. They would pop up directly beneath the Tomcat's orbit, briefly illuminate the F-14 with its radar, and fire one or two air-to-air missiles at it. Iran lost several Tomcats this way.